Exp109



=Objective= To synthesize a [|Ugi adduct] from [|benzaldehyde], [|5-(Trifluoromethyl)-2-furylmethylamine], [|benzylisocyanide] and [|Boc-Gly-OH] in methanol using Ugi 4CR.

=Procedure= A solution of [|benzaldehyde] (106mg, 106uL, 1.04 mmol) and [|5-(Trifluoromethyl)-2-furylmethylamine] (167mg, 1.01mmol) was prepared in methanol-d4 in a 1mL volumetric flask to form an imine overnight. The next day a solution of [|Boc-Gly-OH](175 mg, 1 mmol), and[| benzylisocyanide] (120uL, 1mmol) made up in a 1ml volumetric flask in methanol was added to the preformed imine. The product was filtered and washed with ice cold methanol (5mL).

=Results= [|H NMR (CD3OD)] [|C NMR] [|H NMR] [|C NMR] [|H NMR] [CH2- 4.6 ppm (t) J=2.2Hz, aromatics- 7.3 - 7.4 ppm (broad multiplet)] [|C NMR] [CH2 (t)-46 ppm(J=28Hz), aromatics 127.9-134.5, Isonitrile Carbon (t)-157 ppm(J=22Hz)] [|HNMR] [|Image] [|CNMR]
 * Benzaldehyde**
 * Boc-Gly-OH**
 * Benzyl isocyanide**
 * 5-(Trifluoromethyl)-2-furylmethylamine**

[|t = 3min] [|t = 4min] [|t = 11min] [|t = 37min] [|t = 44min] [|t = 1h15min] [|t = 2h 00min] [|t = 3h 4min] [|t = 17h 3min] [|t = 10min] [|HNMR] [|CNMR] [|image] FAB MS [|High Res] [|Low Res] =Discussion= The NMR and MS data confirms the formation of a Ugi product - =Conclusion= A Ugi product was isolated in 31% yield. =Log=
 * 109A**
 * 109B**
 * 109C**

2007-06-24
14:00 Made up a solution of 5-(Trifluoromethyl)-2-furylmethylamine (167mg) in methanol-d4 in a 1ml volumetric flask, transferred the solution to an NMR tube and obtained HNMR and CNMR. 17:46 Added benzaldehyde (106uL, 1mmol) to the NMR tube containing 1M solution of the amine, this is **109A** 17:49 Obtained HNMR of 109A (t = 3min) 17:50 Obtained HNMR of 109A (t = 4min) 18:01 Obtained HNMR of 109A (t = 11min) 18:23 Obtained HNMR of 109A (t = 37min) 18:30 Obtained HNMR of 109A (t = 44min) 19:01 Obtained HNMR of 109A (t = 01h15min) 19:46 Obtained HNMR of 109A (t = 02h) 20:50 Obtained HNMR of 109A (t = 03h 4min)

2007-06-25
10:49 Obtained HNMR of 109A (t = 17h 3min) 13:45 Made up a solution of benzyl isocyanide (120uL, 1mmol) and Boc-Glycine (175mg, 1mmol) in CD3OD (1ml) 13:49 Added the isocyanide and amino acid solution in the NMR tube containing 109A to form **109B** 13:59 Obtained HNMR of 109B (t = 10min) 14:05 Soon after removing the NMR tube from the NMR instrument, [|solid particles] started to develop in the NMR tube.

2007-06-26
19:20 Almost half of the NMR tube is now filled with the [|solid].

2007-06-27
17:25 After the entire nmr tube was filled with solid, the solid was forced out, washed with methanol, filtered through a sintered glass funnel. The obtained solid was air dried. The remaining mother liquor (**109D**) was saved to recover more product. 19:30 A white solid product **109C** (170mg) [31.16% yield] was obtained.

2007-07-02
08:10 Obtained C NMR of 109C

=Tags= [|[5-(Trifluoromethyl)-2-furylmethylamine] [|InChI=1/C6H6F3NO/c7-6(8,9)5-2-1-4(3-10)11-5/h1-2H,3,10H2] [|Benzaldehyde] [|InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H] [|Boc-Gly-OH] [|InChI=1/C7H13NO4/c1-7(2,3)12-6(11)8-4-5(9)10/h4H2,1-3H3,(H,8,11)(H,9,10)] [|Benzylisocyanide] [|InChI=1/C8H7N/c1-9-7-8-5-3-2-4-6-8/h2-6H,7H2] [|UgiExp109] [|InChI=1/C28H30F3N3O5/c1-27(2,3)39-26(37)33-17-23(35)34(18-21-14-15-22(38-21)28(29,30)31)24(20-12-8-5-9-13-20)25(36)32-16-19-10-6-4-7-11-19/h4-15,24H,16-18H2,1-3H3,(H,32,36)(H,33,37)]

media type="custom" key="91443"