Exp158

=Objective= To synthesize a Ugi adduct from 4-chlorobenzaldehyde, tosylmethyl isocyanide, 5-methylfurfurylamine, and salicylic acid in methanol using Ugi 4CR following Explan005. The target compound was ranked 16 in the [|DEXP014-V1B] 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 a one dram vial, charged with methanol (1mL) 5-methylfurfurylamine, 4-chlorobenzaldehyde, salicylic acid and tosylmethyl isocyanide (0.5mmol each) was added in that order. After each addition, the resulting solution was vortexed for at least 15 seconds and confirmed that a homogeneous solution had been obtained. The vial was capped tight and left at room temperature for 1 day.

(density=0.997g/ml) || 0.5mmol, 69.06mg || 0.5mmol, 96.6 mg ||  ||
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 158/16 || Methanol || 4-chlorobenzaldehyde || 5-methylfurfuryl amine || Salicylic Acid || tosylmethyl isocyanide || no ||
 * Quantity || 1000uL || 0.5 mmol, 70.3 mg || 0.5mmol, 55.7uL

Density information found on the Sigma-Aldrich website (www.sigmaaldrich.com)

=Results=

all components (158A)** || **One day after mixing all components (158B)** || =Discussion=
 * **5 min after mixing
 * [[image:Exp158day1.jpg width="128" height="94" link="http://usefulchem.wikispaces.com/space/showimage/Exp158day1.JPG"]] || [[image:Exp158day2.JPG width="132" height="98" link="http://usefulchem.wikispaces.com/space/showimage/Exp158day2.JPG"]] ||

All results are recorded Master Table and Workflow Tables.

=Conclusion=

After the vial set out at room temperature for a day and was sonicated, no Ugi product was formed.

=Log=

2008-01-17
16:55- Charged a vial with 1 mL of methanol. 17:01- Started to weigh out 4-chlorobenzaldehyde. 17:06- Started to weigh out salicylic acid. 17:10- Started to weigh out tosylmethyl isocyanide. 17:15- Added the 5-methylfurfurylamine to the vial and vortexed for 15 seconds. A clear solution was obtained. 17:17- Added the 4-chlorobenzaldehyde to the vial and vortexed for 15 seconds. A clear solution was obtained. 17:19- Added the salicylic acid to the vial and vortexed for 15 seconds. A clear solution was obtained. 17:22- Added the tosylmethyl isocyanide to the vial and vortexed for one minute. A clear solution was obtained. 17:25- A photo was taken after all of the components were mixed. The solution was left to sit for a day at room temperature.

17:33- Took picture of the vial. No precipitate has formed yet. The solution was very dark green 17:35- Put the vial into the sonicator for ten minutes. 17:45- Removed the vial from the sonicator. No precipitate has formed.
 * 2008-01-18**

=Tags=

[| 4-chlorobenzaldehyde] [|tosylmethyl isocyanide] [|InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3] InChIKey: [|CFOAUYCPAUGDFF]-[|UHFFFAOYAC] [|5-methylfurfurylamine] [|InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3] InChIKey: [|YSEAGSCGERFGBL]-[|UHFFFAOYAH] [|salicylic acid] [| InChI=1/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)] InChIKey: [|YGSDEFSMJLZEOE]-[|UHFFFAOYAQ]