Exp113

== =Objective= To synthesize the [|Ugi product] (086B)from [|benzaldehyde], [|5-methylfurfurylamine],[| tert-butyl isocyanide] and [|Boc-Gly-OH] in methanol via a 4CR Ugi reaction using the Eppendorf protocol (EXPLAN005) =Procedure= To a 1.5 mL Eppendorf tube were added methanol (500 uL), [|5-methylfurfurylamine](5-MFA) (56 uL, 0.5 mmol), [|benzaldehyde] (51 uL, 0.5 mmol), [|Boc-Gly-OH](88 mg, 0.5 mmol), and [|tert-butyl isocyanide] (57 uL, 0.5 mmol). The compounds were added in that order, with a 15 s vortexing (Fisher Vortex Genie 2) after each addition. After 24 hours, a solid formed and the tube was vortexed for 15 s then centrifuged at 14000 RPM for 60 s.This process will continue two more times, with the addition of methanol (500uL) each time before mixing. The resulting solution will be put under high vac in the opened tube.
 * Characterization of 113B**:(C25H35N3O5) White crystals; HNMR ([[image:http://pubs.acs.org/images/gifchars/delta.gif]] ppm, CDCl3) 1.32 (s, 9H), 1.44 (s, 9H), 2.12 (s, 3H), 4.19 (s, 2H), 4.43 (s, 2H), 5.48 (s, 1H), 5.57 (s, 1H), 5.68 (s, 1H), 5.72 (s, 1H), 5.84 (s, 1H), 7.28 (s, 5H). Yield = 31%

=Results= [|H NMR] [|C NMR] [|H NMR] [|C NMR] [|H NMR] [|C NMR] [|H NMR] [|C NMR]
 * Benzaldehyde**
 * 5-methylfurfurylamine**
 * tert-butyl isocyanide**
 * Boc-Gly-OH**

[|HNMR] **//(still wet with methanol and acetone- let dry on high vac in vial (note pressure))//** [|HNMR](**//no acetone but still wet with methanol - re-evaporate under high vac, measuring pressure//**) =Discussion=
 * 113A**
 * 113B**

=Conclusion= A synthesis of the ugi product was successfully accomplished.

=Log=

2007-07-17
13:55 Weighed 1.5mL Eppendorf tube (837.6mg) and labeled it 14:00 Filled tube with methanol (500uL), solution was clear 14:02 Measured 5-methylfufurylamine (56uL) and added it to solution, solution was light orange and translucent 14:03 Mechanically mixed on vortex for 15 seconds 14:04 Measured benzaldehyde (51uL) and added it to solution 14:05 Mechanically mixed on vortex for 15 seconds 14:09 Weighed out 88 mg of Boc-Gly-OH 14:10 Added Boc-Gly-OH to solution, solution turned a dark orange color 14:10 Mechanically mixed on vortex for 15 seconds 14:12 Measured tert-butyl isocyanide (57uL) and added it to solution, solution turned a red-orange color 14:13 Mechanically mixed on vortex for 15 seconds 14:13 Allowed the solution to sit undisturbed in the 1.5mL Eppendorf tube 14:45 Observed white crystals formed along the sides of the Eppendorf tube

2007-07-18
13:30 White crystals formed throughout Eppendorf tube 14:40 Precipitate formed, mixed on vortex for 15 seconds 14:45 Centrifuged at 14000 RPM for 60 seconds, then discarded supernatant 14:48 Added methanol (500uL), mechanically mixed on vortex for 15 seconds 14:50 Centrifuged at 14000 RPM for 60 seconds, then discarded supernatant 14:53 Added methanol (500uL), mechanically mixed on vortex for 15 seconds 14:55 Centrifuged at 14000 RPM for 60 seconds, then discarded supernatant 15:05 Put open tube under high vac (**//pressure//**?) 15:40 Weighed tube, came out to 1011mg 16:00 Emptied tube, laid out contents on filter paper to dry (**//113A//**) **//the powder was still wet after 35 mins on the high vac?//**

2007-07-19
14:35 Placed 0.01g of solid product into an NMR tube with CDCl3 (600uL) 14:40 Obtained an H NMR 16:30 Added the remaining product (0.093g) to the NMR tube

2007-07-20
17:00 Poured solution from the NMR tube into a vial, covered with aluminium foil and poked holes at the top

2007-07-23
11:14 Observed a dry solution in the vial, placed vial into high vac (pressure: ) 12:15 Turned off high vac 15:36 Weighed vial with product (4.751g) 15:55 Washed vial with CDCl3 (800uL) and inserted remaining solution into an NMR tube (solid product from vial included, weighing 0.0714g) 16:05 Weighed empty vial (4.6796g)

=Tags= [|86B][|InChI=1/C25H35N3O5/c1-17-13-14-19(32-17)16-28(20(29)15-26-23(31)33-25(5,6)7) 21(18-11-9-8-10-12-18)22(30)27-24(2,3)4/h8-14,21H,15-16H2,1-7H3,(H,26,31)(H,27,30)] [|benzaldehyde][|InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H] [|5-methylfurfurylamine] [|InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3] [|tert-butyl isocyanide][|InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3] [|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)]