Exp151

=Objective= To synthesize one Ugi product following the EXPLAN005. The compound will contribute toward a library for Falcipain2 inhibitors. This compound was ranked 10 in the [|D-EXP014-V2B] file from the D-EXP014. =Procedure= As described in Explan005 One Ugi reaction was carried out in a dram vial labeled Exp 151-1. To one dram vial was added methanol (250 ul), 3,4 dihydroxybenzaldehyde (0.25mmol, 34.5mg), Methylamine (in a 2M methanolic solution, yielding 125 ul for 0.25 mmol), 2,4,6 Trihydroxbenzoic acid(0.25mmol, 47.0mg), and Tosylmethyl isocyanide (0.25mmol, 38.8mg), in that order. After each addition, the solution was vortexed for 15s and made sure a homogeneous solution was obtained. The formation or absence of precipitate was noted. The dram vial was left at room temperature.

(0.25mmol, 34.5mg) || Methylamine [Methylamine in form of 2M methanolic solution, 0.25 mmol equivalent to 125 ul] || 2,4,6 trihydroxybenzoic acid (0.25mmol, 47.0mg) || Tosylmethyl isocyanide (0.25mmol, 38.8mg) || No ||
 * Compd Id/Rank || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt :yes/no ||
 * 151-1/10 || 3,4 dihydroxybenzaldehyde

=Results= All results are recorded in the [|Master Table of all Ugi synthesis attempts]

Photo of 151-1-A taken at 14:46 immediately after adding all components:

= = Photo of 151-1-B taken at 19:00 the following day,approximately 28 hours following addition of all components: =Discussion=

No precipitate formation was visible upon viewing the sample the day after addition of all components.

=Conclusion=

It is rather difficult to come to any conclusions regarding this experiment besides the fact that these organic compounds were not able to form a precipitate. The Ugi product may have formed but was too soluble in methanol.

=Log=

2007-11-26
14:25: Weighed out aldehyde, acid, and isocyanide on weighing paper 14:30: Added methanol (250uL) into the dram vials, followed by 15 seconds vortexing. 14:32: Added aldehyde into the dram vials, followed by 15 seconds vortexing. 14:34: Added amine into the dram vials, followed by 15 second vortexing. 1436: Added acid into the dram vials followed by 15 second vortexing 14:40: Added isocyanide into dram vials followed by 15 second vortexing. 14:45: Let vial sit in fume hood overnight 14:46: Took pic of 151-1-A.

2007-11-27
19:00: Checked vial and no precipitate found. 19:00: Took pic of 151-1-B.

=Tags= [|Methylamine] [|InChI=1/CH5N/c1-2/h2H2,1H3] [|Tosylmethyl isocyanide] [|InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3] [|3,4 dihydroxybenzaldehyde] [|InChI=1/C7H6O3/c8-4-5-2-1-3-6(9)7(5)10/h1-4,9-10H] [|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)/f/h11H]