Exp114



=Objective= To synthesize a Ugi adduct from furfuraldehyde, methylamine, benzylisocyanide and α,4-dimethylphenylacetic acid following the EXPLAN005 in methanol. =Procedure= To a 2.0M solution of methylamine in methanol (250ul, 0.5 mmol) was added methanol (250uL) furfuraldehyde (41.5uL, 0.5 mmol), α,4-Dimethylphenylacetic acid (82.1mg, 0.5 mmol) and benzylisocyanide (60.5uL, 0.5 mmol) in a 1.5 ml Eppendorf tube in that order, with 15 s mixing after each addition. The reaction mixture was left undisturbed overnight. The solution was then vortexed and centrifuged. The residue was washed successively with methanol (2 **//the protocol calls for 3 washes//** x 500uL), centrifuged and dried under vacuum. =Results=

Characterization of 114A
brown solid, 7.2 mg [|HNMR] (however sparingly soluble in CDCl3) =Discussion= The small amount of brown precipitate obtained after methanol washes was sparingly soluble in CDCl3, which is uncharacteristic of the typical Ugi products we have obtained in the past. Either the Ugi product is too soluble in methanol and was washed away or the reaction did not proceed.

=Conclusion= The Ugi product was not isolated.

=Log=

2007-07-24
15:10 Weighed Eppendorf tube (0.8271g) and labeled 15:14 Added methanol (250uL) to tube 15:15 Added methylamine (250uL) to tube and vortexed for 15 s 15:17 Added furfuraldehyde (41.5uL) to solution and vortexed for 15 s, observed orange solution 15:19 Added α,4-Dimethylphenylacetic acid (82.1mg) to solution and vortexed for 15 s 15:21 Added benzylisocyanide (60.5uL) to solution and vortexed for 15 s, observed brown color, all compounds dissolved 15:24 Placed under fume hood to sit undisturbed overnight 16:17 Observed solution with about half appearing as a brown solid in the Eppendorf tube

2007-07-25
11:00 Observed brown solid on the bottom of tube, a lighter brown solid formed above this, and the remaining purple colored liquid 11:20 Mixed tube on vortex for 15 seconds 11:30 Centrifuged at 14000 RPM for 60 seconds, then discarded supernatant 11:33 Added methanol (500uL), mechanically mixed on vortex for 15 seconds 11:35 Centrifuged at 14000 RPM for 60 seconds, then discarded supernatant 11:38 Added methanol (500uL), mechanically mixed on vortex for 15 seconds 11:40 Centrifuged at 14000 RPM for 60 seconds, then discarded supernatant 11:45 Put open tube under vacuum with 7mm pressure 14:45 Took Eppendorf tube with a solid out of the vacuum, weighed it (.8343g) 15:44 Took H NMR of brown solid partially dissolved in CDCl3 (800uL) [There was solid still hanging in the nmr tube]