Objective

To synthesize12 Ugi adducts using Ugi 4CR .The target compound were ranked 1-12 in the DEXP014-V2B file from D-EXP014. The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this summary post

Procedure

To twelve vials, labeled 1-12 and charged with methanol (4 ml), the four reactants [aldehyde, amine, acid and isocyanide] (1mmol each) were added to each in that order. After each addition, the resulting solution was vortexed for 15 seconds (or more) and confirmed that a homogeneous solution had been obtained. The vials were capped tight and left at room temperature. After crystallization, each solution was decanted and the crystals were washed with methanol (3x 500uL) and dried under vacuum to obtain yields reported in the table.
171F/6-4: N-[2-(tert-butylamino)-1-(2-naphthyl)-2-oxo-ethyl]-N-methyl-4-pyr​en-1-yl-butanamide; C37H36N2O2; White solid; M.Pt: 155-157 C; 1H NMR (external image delta.gif ppm, CDCl3) 1.37 (s, 9H), 2.79 (s, 3H), 2.19 (m, 2H), 2.44 (m, 2H), 3.34 (m, 2H), 5.95 (bs, 1H) 6.49 (s,1H), 7.30-8.45 (aromatics, 16H) 13C NMR (external image delta.gif ppm, CDCl3) ppm, 26.6, 28.6, 32.4, 32.6, 32.9, 51.6, 60.4, 123.3, 124.5, 124.66, 124.68, 124.8, 124.9, 125.6, 126.3, 126.41, 126.48, 126.5, 127.1, 127.2, 127.3, 127.4, 127.9, 128.3, 128.4, 128.6, 129.7, 130.7, 131.2, 132.7,133.0, 133.2, 136.0, 169.1, 173.5 ; HRMS (FAB,m-nitrobenzyl alcohol): m/z calcd for C37H37N2O2 541.28550 (M+H) found 541.2856.
171K/11-4: N-[2-(tert-butylamino)-1-(4-dimethylaminophenyl)-2-oxo-ethyl]-N-m​ethyl-4-pyren-1-yl-butanamide; C35H39N3O2; White solid; M.Pt: 193-195 C; 1H NMR (external image delta.gif ppm, CDCl3) 1.35 (s, 9H), 2.25 (m, 2H), 2.47 (m, 2H), 2.76 (s, 3H), 2.92 (s, 6H), 3.42 (m, 2H), 5.55 (bs 1H, Labile), 6.18 (s, 1H), 6.66 (d, 2H, J = 8.8 Hz), 7.19 (d, 2H , J = 8.8 Hz), 7.77-8.40 (Pyrenyl Aromatics, 9H); 13C NMR (external image delta.gif ppm, CDCl3) ppm, 26.6, 28.6, 32.1, 32.6, 33.0, 40.2, 51.4, 60.1, 112.2, 123.4, 124.5, 124.64, 124.66, 124.8, 124.9, 125.6, 126.4, 127.1, 127.30, 127.37, 128.6, 129.6, 130.1, 130.8, 131.2, 136.2, 149.9, 169.7, 173.1 ; HRMS (FAB,m-nitrobenzyl alcohol): m/z calcd for C35H39N3O2Na 556.2939 (M+Na) found 556.2935

V2B Rank/ExpID
Solvent Methanol
Aldehyde
Amine
Acid
Isocyanide
Ppt (Y/N) & Yield
1/ 171A
4ml
4,7-dimethoxy-1-
naphthaldehyde (216.23mg)
methylamine (500uL)
2,3-.dihydroxybenzoic acid (154.12mg)
Tosylmethyl
isocyanide (195.24mg)
Y
2/171B
4ml
2-hydroxy-3-methoxy
benzaldehyde (152.15mg)
5-methylfurfuryl
amine (111.4uL)
Pyrene-1-butyric acid (288.34mg); HNMR
t-butyl
isocyanide (113.10uL)
N
3/171C
4ml
Phenanthrene-9-
carboxaldehyde (206.24mg)
methylamine (500uL)
2,4,6-trihydroxybenzoic acid (188.13mg)
Tosylmethyl
isocyanide (195.24mg)
Reactants insoluble in methanol at this concentration
4/171D
4ml
2-hydroxy-3-methoxy
benzaldehyde (152.15mg)
Benzylamine (109.22uL)
Pyrene-1-butyric acid (288.34mg)
t-butyl
isocyanide
(113.10uL)
Y
5/171E
4ml
2-hydroxy
benzaldehyde (106.5uL)
3-chloroaniline (105.77uL)
3,4-methylenedioxy
phenylacetic acid (180.16mg)
Tosylmethyl
isocyanide (195.24mg)
Reactants not completely soluble in methanol at this concentration
6/171F
4ml
2-naphthaldehyde (156.18mg)
methylamine (500uL)
Pyrene-1-butyric acid (288.34mg)
t-butyl
isocyanide
(113.10uL)
Y
Yield : 26%
7/171G
4ml
2-naphthaldehyde (156.18mg)
furfurylamine (88.37uL)
3,4-dihydroxy
phenylacetic acid (168.15mg)
Tosylmethyl
isocyanide (195.24mg)
N
8/171H
4ml
3,5-dimethoxy
benzaldehyde; HNMR (166.17 mg)
methylamine (500uL)
2,4,6-trihydroxybenzoic acid (188.13mg)
Tosylmethyl
isocyanide (195.24mg)
Y
9/171I
4ml
2-hydroxybenzaldehyde (106.5uL)
Aniline
(91.1uL)
3,4-methylenedioxy
phenylacetic acid (180.16mg)
Tosylmethyl
isocyanide (195.24mg)
N
10/171J
4ml
3,4-dihydroxy
benzaldehyde (138.12mg)
methylamine (500uL)
2,4,6-trihydroxybenzoic acid (188.13mg)
Tosylmethyl
isocyanide (195.24mg)
N
11/171K
4ml
4-(Dimethylamino)
benzaldehyde (149.19mg)
methylamine (500uL)
Pyrene-1-butyric acid (288.34mg)
t-butyl
isocyanide
(113.10uL)
Y
Yield : 53%
12/171L
4ml
Phenanthrene-9-
carboxaldehyde (206.24mg)
methylamine (500uL)
Pyrene-1-butyric acid (288.34mg)
t-butyl
isocyanide
(113.10uL)
Reactants insoluble in methanol at this concentration
Chemical Data in Table of Chemicals

Results

Pictures taken soon after the addition of all reactants.
171A/1
171B/2
171C/3
171D/4
171E/5
171F/6
171G/7
171H/8
171I/9
171J/10
171K/11
171L/12
171A-1.JPG
171B-2-1.JPG
171C-3.JPG
171D-4.JPG
171E-5.JPG
171F-6.JPG
171G-7.JPG
171H-8.JPG
171I-9.JPG
171J-10.JPG
171K-11.JPG
171L-12.JPG
8th day
8th day
8th day
8th day
8th day
8th day
8th day
8th day
8th day
8th day
8th day
8th day
171A-1.JPG
171-B-2.JPG
171C-2.JPG
171D-2.JPG
171E-2.JPG
171F-2.JPG
171G-2.JPG
171H-2.JPG
171I-2.JPG
171J-2.JPG
171K-2.JPG
171L-2.JPG
171A-10thday.JPG
No Ppt
Reactants
insoluble
171-D-3.JPG
Reactants
insoluble
171F-11thday.JPG
No Ppt
171H-10thday.JPG
No Ppt
No Ppt
171K-10thday.JPG
Reactants
insoluble
10th day
ISOLATED
Aborted
Aborted
9th day
ISOLATED
Aborted
11th day
ISOLATED
Aborted
10th day
ISOLATED
Aborted
Aborted
10th day
ISOLATED
Aborted

Characterization of 171A/1-4
Amount: 24.5mg
  1. HNMR
  2. HNMR [H-Exchange with methanol-d4]
  3. Overlay [with labile H Vs Exchanged]
  4. CNMR

Characterization of 171D/4-4

Amount: 63mg [only slightly soluble in CDCl3, Acetone-D6 & Benzene-D6]
  1. Melting Point :191-193 C
  2. IR
  3. HNMR
  4. HNMR [H-Exchange with methanol-d4]
  5. Overlay [with labile H Vs Exchanged]
  6. CNMR
  7. FAB-MS- I, FAB-MS- II (Nominal mass)

Characterization of 171F/6-4

Amount: 139mg ; Yield - 25.7%
  1. Melting Point : 155-157 C
  2. IR
  3. HNMR
  4. HNMR [H-Exchange with methanol-d4]
  5. Overlay [with labile H Vs Exchanged]
  6. CNMR
  7. FAB-MS (Nominal Mass)
  8. FAB-MS (Exact Mass)

Characterization of 171H/8-4

Amount: 170mg
  1. Melting Point: 243-247 C
  2. IR(KBr Pellet)
  3. HNMR
  4. HNMR [H-Exchange with methanol-d4]
  5. Overlay [with labile H Vs Exchanged]
  6. CNMR[in DMSO-D6 & CD3OD]
  7. FAB-MS (Nominal Mass)
  8. MS/MS

Characterization of 171K/11-4

Amount: 283mg; Yield: 53.0 %
  1. IR
  2. HNMR
  3. HNMR [H-Exchange with methanol-d4]
  4. Overlay [with labile H Vs Exchanged]
  5. CNMR
  6. FAB-MS (Nominal Mass)
  7. FAB-MS (Exact Mass)


Discussion

  • It is interesting to note that the reactants which were insoluble initially (171B/2, 171D/4, 171E/5, 171F/6) went into solution after 9 days.
  • 171A/1-4
NMR - Proton NMR : Peaks corresponding to the two methoxys (on naphthyl) can be seen at 3.9 and 4.0 ppm, however they are surrounded by other peaks, indicating the presence of other dimethoxy naphthyl impurities. This pattern is with respect to almost all peaks. for example N-methyl at 3.4 ppm and the aromatic region. This is supported by the integrations for the peaks which clearly indicate more than required number of protons for a ugi product. Precipitation of impurities may be attributed to the delayed isolation of the product which could have resulted from loss of solvent methanol over a period of time. Therefore 171A/1-4 would have to have be synthesized again.
IR - Indicates the presence of a carbonyl (1687 cm-1), labile protons (on O /N) present ( 3100-3200 cm-1).
NMR - Proton NMR (in DMSO-d6) shows a quintet accounting for 2H at 2.04 ppm, a triplet at 2.43 ppm for 2H and another triplet at 3.36 ppm integrating for 2H. The aromatic region integrates for around 9H. Also an exchangeable proton (with methanol-d4) is present at 12.21 ppm. The proton NMR of 171D, clearly proves that Pyrene-1-butyric acid, a starting material has been isolated. The acid may have precipitated back from the reaction mixture over a period of time.
FAB-MS - The mass definitely nails the acid at m/z 289 for m+1 ion and m+ ion at m/z-288.
IR - Intense hydrocarbon (C-H) absorbance, carbonyl at 1635 cm-1.
NMR - Proton NMR: Singlet at 1.37 ppm which integrates for 9H can be assigned to a t-butyl group (from t-butyl isocyanide), singlet at 2.79 ppm integrating for 3H can be assigned to N-methyl (coming from methylamine), multiplet at 2.19, 2.44 and 3.34, accounting for 2H each can be attributed to the three diasterotopic methylenes connected to pyrene (coming from Pyrene-1-butyric acid) [matches predicted HNMR; ChemDraw Ultra]. A broad singlet at 5.95 ppm accounting for 1H (to be confirmed, if is labile) can be assigned to the NH (sec.amide), another singlet at 6.49 ppm integrating for 1H can be assigned to the enantiomeric proton. The aromatic region (7.3-8.45 ppm) accounts for a total of 16H, confirming the isolation of a pure Ugi product for 171F. Tentative HNMR assignments (non aromatic only)
CNMR - C13 confirms the the presence of a ugi product by accounting for all non equivalent carbons (all except t-butyl) in the molecule.
FAB-MS - Shows M+ ion at 540.4 (Nominal mass) and 563.2676 for M+Na and 541.2856 for M+H in HRMS.
IR - Overwhelmed by the H-bonded phenolic OH. There may also be the N-H (primary amide) stretching band in the same range. The Ugi dipeptide contains two carbonyls, supported by an intense absorbance at ~1610 cm-1, but this may as well be assigned to the carbonyl of the acid ( if unreacted), but it is inconceivable that the acid could have survived the three methanol washes.- Although the IR does not conclusively confirm the assigned structure, it does not contradict it and it is consistent with the ugi adduct 171H.
NMR - 171H/8-4 was only slightly soluble in CDCl3, Acetone-D6, D2O & Benzene-D6, however it was soluble in DMSO-D6.
Proton NMR: Indicates the presence of dimethoxy [6H at 3.72 PPM], suggesting the presence of 3,5-dimethoxybenzene in the product. The HNMR also shows a 3H labile peak at 8.95PPM indicating the presence of the trihydroxybenzene component in the product. A 3H methyl peak is also seen at 3.36PPM, possibly from methyl amine. Off the four components the one missing is Tosylmethyl isocyanide. Tosyl ring should have given two clear doublet of doublet in the aromatic region. This is missing. Therefore the HNMR rules out the possibility of a ugi product in the sample.
C-NMR - Only 13 peaks are seen, confirming an absence of tosylmethyl group.
FAB-MS - Observed peaks : Protonated parent ion (M+H= 349.34), loss of a methoxy group (m/z -319.1) followed by a further loss of a water molecule (m/z- 301.1). FAB-MS supports the imminium benzoate structure for
Based on the information obtained from IR, HNMR, CNMR and FAB-MS ; a structure of an imminium benzoate can be assigned to 171H/8-4. A cyclization via an OH oxygen would break the equivalence of the acid derived aromatic protons and would not still give a parent ion mass at 349, but would not fit the HNMR pattern.
IR - Indicates the presence of a carbonyl (1625 cm-1), labile protons (on O /N) present ( 3100-3200 cm-1) and C-H absorbance (2900-3300 cm-1)
NMR- Proton NMR of 1717K is consistent with a corresponding Ugi product. A singlet at 1.35 integrates for 9H, this can be assigned to the t-butyl group (from t-butyl isocyanide), three multiplets at 2.25, 2.27 and 3.42 ppm account for 2 H each, assigned to three methylene groups connected to the pyrene (from Pyrene-1-butyric acid), a singlet at 2.79 ppm integrates for 3H attributed as N-methyl (from methyl amine), another singlet at 2.92 ppm integrating for 6H can be assigned to the two equivalent N,N-dimethyl (from 4-(Dimethylamino) benzaldehyde). A broad singlet at 5.55 ppm accounts for 1H, assigned as the single amide proton, confirmed by a deuterium exchange experiment by adding methanol-d4. The chiral (enantiomeric) proton appears as a singlet at 6.18 ppm. Two sets ortho and meta protons on the phenyl ring (from aldehyde) appear at 6.66 and 7.19 ppm (J= 8.8Hz). The remaining 9H pyrenyl protons appear between 7.77 and 8.4 ppm. In effect HNMR confirms 171K as a Ugi product.
FAB-MS- Shows an M+Na at 555.2936 (HRMS) and 1067.3 for 2M+H (Nominal mass)

Conclusion

Only two ugi adducts were successfully synthesized.

Log

2008-02-21

18:00 Weighed all the solid aldehydes (1mmol).
19:00 Made up a solutions of all aldehydes in methanol (4ml). Notes:4,7-dimethoxynaphthaldehyde (171A/1) took 8 min of vortexing to completely dissolve, 2-naphthaldehyde (171F/6 and 171G/7) took 1 min of vortexing to completely dissolve in methanol. Phenanthrene-9-carboxaldehyde (171C/3 and 171L/12) did not go in solution even after 10 min vortexing. Remaining aldehydes easily dissolved in methanol after a 15s vortex.
21:30 Weighed all the solid reactants, all acids and tosylmethyl isocyanide.
21:40 Started adding respective amines to the vials (some with undissolved aldehydes in them), vortexed each for 15s.
22:30 Started adding acids to each vial, reactants in vials 171B/2, 171C/3, 171D/4,171E/5,171F/6, 171L/12 did not go in solution even after vortexing for 3 mins each.
23:30 Completed adding respective isocyanides to each vial. Vortexed for 15s each. Obtained pictures of the solutions; 171A-D; 171D-G; 171G-L.

2008-02-22

19:30 Nothing has changed physically in any of the vials. The solutions which were clear yesterday remain clear and the ones which contained insolubilized reactants remain unchanged.

2008-02-23

10:52 Still no change.
13:22 Obtained a picture of all clear solutions
13:29 Started to sonicate the clear solutions for 10 min inorder to induce crystallization.
13:39 Stopped sonicating.
13:56 Obtained a picture of the previously clear solutions, crystallization has started in 171H/8, this solution is now called 171H-2/8 (no need to relabel the vial - this is still 171H but you do need to clearly label all the pics you take)
20:26 Obtained a picture again.

2008-02-24

16:00 Added an 1ml of chloroform to 3/171C, 4/171-D, 5/171E, 12/171L vortexed for 3mins in order to dissolve the reactants, nothing dissolved, therefore added 1ml of methanol to the above mentioned three solutions...still nothing changed
16:30 Added 1ml of chloroform to 6/171F, vortexed for 3min, solution cleared.

2008-02-29

17:30 Obtained pictures of the solutions.

2008-03-01

20:00 Observed beautiful crystals develop in the vial - 171D/4

2008-03-02

16:10 Observed solid in 171A/1

2008-03-03

14:10 Observed solid in 171F/6

2008-03-20

16:00 The methanolic solution from the crystalline products 171K/11-3 was decanted. To the solid in the vial, methanol (1ml) was added, vortexed, transferred to a pre-weighed small vial and centrifuged. The supernatant was decanted. The solid was washed with methanol (2 x 1ml). A total of three methanol washes were performed.
19:40 The solid obtained after the decanting the supernatant was set under a high vac.
22:30 Removed the products from the high vac and stored them uncapped in a desiccator set under house vac. The products are now renamed as 171K/11-4

2008-03-21

14:30 Obtained
  • 171K/11-4 -- 283mg

2008-03-23

21:33 Obtained HNMR of 171K11-4 (This HNMR has phasing issues, therefore another one was obtained on 04-21-08- see log below)

2008-03-25

11:00 The methanolic solution from the precipitates 171A/1-3, 171D/4-3,171F/6-3, and 171H/8-3 were vortexed for 15s, centrifuged and the supernatant was decanted to another vial. To the solid in the vial, methanol (1ml) was added, vortexed 15s, transferred to a pre-weighed small vial and centrifuged. The supernatant was collected with the previous supernatant. The solid was washed with methanol (2 x 1ml). A total of three methanol washes were performed.
14:40 The solid obtained after the decanting the supernatant was set under a high vac.
21:30 Turned off the high vac and connected the desiccator to house vac.

2008-03-26

11:30 Obtained 171A/1-4 (24.5mg) from 171A/1-3; 171D/4-4 (63mg) from 171D/4-4; 171F/6-4 (139mg) from 171F/6-3; and 171H/8-4 (170mg) from 171H/8-3.

2008-03-27

10:46 Obtained HNMR of 171F/6-4
14:05 Obtained CNMR of 171F/6-4

2008-03-30

01:45 Obtained HNMR of 171A/1-4

2008-03-31

11:00 Tried dissolving 171D/4-4 and171H/8-4 in acetone d6, with no luck. Evaporated the solvent under N2 gas

2008-04-01

13:00 Tried dissolving 171D/4-4 and171H/8-4 in benzene d6 again, no luck. Set under a gentle flow of N2 to evaporate the solvent.

2008-04-11

16:00 Dissolved 171H-8/4 in DMSO-D6 and obtained a HNMR on 500MHz Varian inova.
17:00 Added methanol-d4 to the above 171H-8/4, DMSO-D6 solution in the NMR and obtained another HNMR; to check the labile proton signal.

2008-04-13

21:00 Obtained C-13 NMR in DMSO-D6.

2008-04-14

12:00 A small amount of 171H (~200mg) in a NMR tube remained insoluble in D2O (1000uL), 1N HCl (~200uL) was added to it, the solid did not dissolve and settled down. Therefore about 2/3 of the supernatant, was pipetted out, and Conc.HCl (~500) was added to the tube. The solid readily dissolved in it. To this CDCl3 was added and the solution was shaken up well. The solution was poured out in to a vial. The bottom CDCl3 layer (171H-Org HNMR) was separated (pipetted out) and a HNMR was obtained. A small portion of top aqueous / acid layer was dissolved in D2O (~800uL) (171H-aq, HNMR overwhelmed by ) and and HNMR was obtained.
13:00 Submitted the sample for MS-FAB analysis.

2008-04-21

16:30 Obtained another HNMR of 171K/11-4 , then added CD3OD (400uL) to exchange any labile proton with deuterium.

2008-04-27

18:20 Obtained HNMR of 171D in DMSO-d6, soon after 100uL of CD3OD was added to the NMR tube and another HNMR was obtained.


Tags

4,7-dimethoxy-1-naphthaldehyde: InChI=1/C13H12O3/c1-15-10-4-5-11-12(7-10)9(8-14)3-6-13(11)16-2/h3-8H,1-2H3 ;Inchi Key: FFAODEUKHYBIKI-UHFFFAOYAI)
2-hydroxy-3-methoxybenzaldehyde: InChI: InChI=1/C8H8O3/c1-11-7-4-2-3-6(5-9)8(7)10/h2-5,10H,1H3 ; InChIKey: JJVNINGBHGBWJH-UHFFFAOYAB
Phenanthrene-9-carboxaldehyde : InChI=1/C15H10O/c16-10-12-9-11-5-1-2-6-13(11)15-8-4-3-7-14(12)15/h1-10H InChIKey: QECIGCMPORCORE-UHFFFAOYAE
2-hydroxybenzaldehyde InChI=1/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H ; InchiKey SMQUZDBALVYZAC-UHFFFAOYAD
2-naphthaldehyde: InChI=1/C11H8O/c12-8-9-5-6-10-3-1-2-4-11(10)7-9/h1-8H ; InchiKeyPJKVFARRVXDXAD-UHFFFAOYAM
3,5-dimethoxybenzaldehyde InChI=1/C9H10O3/c1-11-8-3-7(6-10)4-9(5-8)12-2/h3-6H,1-2H3 : VFZRZRDOXPRTSC InchiKey UHFFFAOYAG
3,4-dihydroxybenzaldehyde: InChI=1/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H InchiKey BGBGRVKPALMCQ-UHFFFAOYAN
4-(Dimethylamino)benzaldehyde: InChI=1/C9H11NO/c1-10(2)9-5-3-8(7-11)4-6-9/h3-7H,1-2H3 ;InchiKey BGNGWHSBYQYVRX-UHFFFAOYAG
methylamine:; InChI=1/CH5N/c1-2/h2H2,1H3 InchiKey BAVYZALUXZFZLV-UHFFFAOYAN
5-methylfurfurylamine InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3 ;InchiKey: YSEAGSCGERFGBL-UHFFFAOYAH
Benzylamine:; InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3 InchiKeyWGQKYBSKWIADBV-UHFFFAOYAL
3-chloroaniline InChI=1/C6H6ClN/c7-5-2-1-3-6(8)4-5/h1-4H,8H2/p+1 ; InChIKey: PNPCRKVUWYDDST-IKLDFBCSAB
furfurylamine:; InChIKey: PNPCRKVUWYDDST-IKLDFBCSABInchiKey DDRPCXLAQZKBJP-UHFFFAOYAX
Aniline; InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2 InchiKey: PAYRUJLWNCNPSJ-UHFFFAOYAP
2,3-dihydroxybenzoic acid; InChI=1/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11) InchiKey: GLDQAMYCGOIJDV-UHFFFAOYAE
Pyrene-1-butyric acid; InChI=1/C2​0H16O2/c21​-18(22)6-2​-3-13-7-8-​16-10-9-14​-4-1-5-15-​11-12-17(1​3)20(16)19​(14)15/h1,​4-5,7-12H,​2-3,6H2,(H​,21,22) InchiKey: QXYRRCOJHNZVDJ-UHFFFAOYAV
3,4-methylenedioxyphenylacetic acid: InChI=1/C9H8O4/c10-9(11)4-6-1-2-7-8(3-6)13-5-12-7/h1-3H,4-5H2,(H,10,11) ;InchiKey ODVLMCWNGKLROU-UHFFFAOYAB
3,4-dihydroxyphenylacetic acid: InChI=1/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) ;InchiKeyCFFZDZCDUFSOFZ-UHFFFAOYAU
2,4,6-trihydroxybenzoic acid: InChI=1/C7H6O5/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2,8-10H,(H,11,12) ;InchiKey IBHWREHFNDMRPR-UHFFFAOYAP
Tosylmethylisocyanide: InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3 ;InchiKey CFOAUYCPAUGDFF-UHFFFAOYAC
t-butylisocyanide: InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3 ;InchiKeyFAGLEPBREOXSAC-UHFFFAOYAL
171A/1-4 InChI=1/C3 ​0H30N2O8S/​c1-18-8-11​-20(12-9-1​8)41(37,38​)17-31-29(​35)27(32(2​ )30(36)23-​6-5-7-25(3​3)28(23)34​)22-14-15-​26(40-4)21​-13-10-19(​ 39-3)16-24​(21)22/h5-​16,27,33-3​4H,17H2,1-​4H3,(H,31,​35); InChIKey: OBFOADZYUAXPQR-UHFFFAOYAI
171D/4-4 InChI=1/C4 ​0H40N2O4/c​1-40(2,3)4​1-39(45)37​(32-16-10-​17-33(46-4​)38(32)44)​ 42(25-26-1​1-6-5-7-12​-26)34(43)​18-9-13-27​-19-20-30-​22-21-28-1​ 4-8-15-29-​23-24-31(2​7)36(30)35​(28)29/h5-​8,10-12,14​-17,19-24,​ 37,44H,9,1​3,18,25H2,​1-4H3,(H,4​1,45) InChIKey: KXVZVKYNUILZLL-UHFFFAOYAU
171F/6-4InChI=1/C3 ​7H36N2O2/c​1-37(2,3)3​8-36(41)35​(30-20-15-​24-9-5-6-1​0-29(24)23​ -30)39(4)3​2(40)14-8-​11-25-16-1​7-28-19-18​-26-12-7-1​3-27-21-22​ -31(25)34(​28)33(26)2​7/h5-7,9-1​0,12-13,15​-23,35H,8,​11,14H2,1-​ 4H3,(H,38,​41) ; InChIKey: NUNVDGNLCJMQCZ-UHFFFAOYAN
171H/8-4InChI=1/C2 ​6H28N2O9S/​c1-15-5-7-​20(8-6-15)​38(34,35)1​4-27-25(32​)24(16-9-1​ 8(36-3)13-​19(10-16)3​7-4)28(2)2​6(33)23-21​(30)11-17(​29)12-22(2​ 3)31/h5-13​,24,29-31H​,14H2,1-4H​3,(H,27,32​) InChIKey: VOMFOJPVEOJWBN-UHFFFAOYAP
171K/11-4 InChI=1/C3 ​5H39N3O2/c​1-35(2,3)3​6-34(40)33​(27-17-20-​28(21-18-2​7)37(4)5)3​ 8(6)30(39)​12-8-9-23-​13-14-26-1​6-15-24-10​-7-11-25-1​9-22-29(23​ )32(26)31(​24)25/h7,1​0-11,13-22​,33H,8-9,1​2H2,1-6H3,​(H,36,40) InChIKey: XWJCEFGKUMNBLK-UHFFFAOYAD