Exp155

=Objective= To synthesize a [|Ugi adduct] (//**wrong link**//) from [|benzaldehyde], [|5-methyl-2-furylmethylamine], [|3-(4-methoxyphenyl)propionic acid], and [|tert-Butyl isocyanide] in methanol using Ugi 4CR following Explan005. The target compound was ranked 159 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 (1 ml), 5-methyl-2-furylmethylamine, benzaldehyde, 3-(4-methoxyphenyl)propionic acid and tert-butyl isocyanide. (0.5mmol each) was added in that order. After each addition, the resulting solution was vortexed for 15 seconds and confirmed that a homogeneous solution had been obtained. The vial was capped tight and left at room temperature.

(density=1.045 g/ml) || 0.5mmol, 55.9ul (density=0.997g/ml) || 0.5mmol, 90.2mg || 0.5mmol, 56.6uL (density=0.735g/ml) ||  || The densities were obtained the the Sigma-Aldrich website ([|www.sigmaaldrich.com])
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 155/159 || Methanol || benzaldehyde || 5-methyl-2-furylmethylamine || 3-(4-methoxyphenyl)propionic acid || tert-butylisocyanide || No ||
 * Quantity || 1000uL || 0.5mmol, 50.78ul

=Results= all components (155A)** ||  || **Approx. 24 hours after mixing all components (155B)** ||
 * **5 min after mixing
 * [[image:Exp155day1.JPG width="169" height="144" link="http://usefulchem.wikispaces.com/space/showimage/Exp155day1.JPG"]] ||  || [[image:Exp155day2.JPG width="171" height="139" link="http://usefulchem.wikispaces.com/space/showimage/Exp155day2.JPG"]] ||


 * **After sonication** ||  ||
 * [[image:Exp155day2a.JPG width="144" height="123" link="http://usefulchem.wikispaces.com/space/showimage/Exp155day2a.JPG"]] ||  ||

=Discussion=

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

=Conclusion=

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

=Log=

15:18- Charged vial with 1ml of methanol 15:23- Weighed out the acid. 15:26- Added amine to vial and vortexed for 15 seconds. A clear solution was achieved. 15:28- Added the aldehyde to the vial and vortexed for 15 seconds. A clear solution was achieved. 15:30- Added acid to the solution and vortexed for 15 seconds and the acid was dissolved. A clear solution was achieved. 15:32- Added isocyanide to the vial and vortexed for 15 seconds. A clear solution was achieved. 15:34- The vial was left to sit at room temperature for a day. The liquid is an amber/brown color. 15:39- Took picture of the vial.
 * 2008-01-10**

15:25- Took picture of the vial. No precipitate has formed yet. 15:38- Put the vial into the sonicator for ten minutes. 15:48- Removed the vial from the sonicator. No precipitate has formed. 15:58- Took another picture of the vial after sonication.
 * 2008-01-11**

=Tags=

[|Benzaldehyde] [|InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H] InChIKey: [|HUMNYLRZRPPJDN]-[|UHFFFAOYAE] [|5-methyl-2-furylmethylamine] [|InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3] InChIKey: [|YSEAGSCGERFGBL]-[|UHFFFAOYAH] [|3-(4-methoxyphenyl)propionic acid] [|InChI=1/C10H12O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-3,5-6H,4,7H2,1H3,(H,11,12)] InChIKey: [|FIUFLISGGHNPSM]-[|UHFFFAOYAL] [|tert-Butyl isocyanide] [|InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3] InChIKey: [|FAGLEPBREOXSAC]-[|UHFFFAOYAL]