Exp156

=Objective= To synthesize a [|Ugi adduct] (//**wrong link**//) from Phenanthrene-9- carboxaldehyde, tert-butyl isocyanide, benzylamine, and crotonic acid in methanol using Ugi 4CR following Explan005. This is a repeat of Exp143c.The target compound was ranked 155 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].

[The experiment is repeated because Phenanthrene-9-carboxaldehyde which was used in the previous experiment was acquired as a liquid. The aldehyde used here was obtained from Sigma Aldrich as a solid- Mpt-100C]

=Procedure= To a one dram vial, charged with methanol (1mL) benzylamine, phenanthrene-9-carboxaldehyde, crotonic 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 for 1 day.

carboxaldehyde || benzylamine || Crotonic acid || tert-butylisocyanide || **Yes** || (density=0.981g/ml) || 0.5mmol, 43.0mg || 0.5mmol, 56.5uL (density=0.735g/ml) ||  ||
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 156/155 || Methanol || Phenanthrene-9-
 * Quantity || 1000uL || 0.5mmol, 103.1mg || 0.5mmol, 56.6uL

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

=Results=

all components (156A)** || **One day after mixing all components (156B)** || =Discussion=
 * **5 min after mixing
 * [[image:Exp156day1.JPG width="120" height="89" link="http://usefulchem.wikispaces.com/space/showimage/Exp156day1.JPG"]] || [[image:Exp156day2.JPG width="129" height="94" link="http://usefulchem.wikispaces.com/space/showimage/Exp156day2.JPG"]] ||

The experiment was repeated because Phenanthrene-9-carboxaldhyde which was used in the previous experiment was obtained as a liquid, the [|HNMR] of the liquid does not correspond to the [|NMR of the compound] purchased from Sigma-Aldrich.

All results are recorded Master Table and Workflow Tables.

=Conclusion=

After one day a precipitate was obtained - analysis by NMR pending to confirm Ugi product.

=Log=

2008-01-11
17:22- Weighed out the Phenanthrene-9-carboxaldehyde. 17:30- Weighed out the crotonic acid. 17:39- Charged a vial with 1 ml of methanol. 17:42- Added the benzylamine to the vial and vortexed for 15 seconds. A clear solution was obtained. 17:44- Added the phenanthrene-9-carboxaldehyde and vortexted for 6 minutes before the solution was no longer cloudy. The solid went into the solution. 17:48- Added the crotonic acid and vortexed for one minute before the solution was not longer cloudy. A clear solution was obtained. 17:50- Added the tert-butyl isocyanide and vortexted for one minute. A clear solution was obtained. 17:55- A photo was taken after all of the components were mixed. The solution was left to sit for a day at room temperature.

17:45- The solution precipitated white crystals. A photo of the vial was taken.
 * 2008-01-12**

=Tags=

[| Phenanthrene-9- carboxaldehyde] [|InChI=1/C15H10O/c16-10-12-9-11-5-1-2-6-13(11)15-8-4-3-7-14(12)15/h1-10H] InChIKey: [|QECIGCMPORCORE]-[|UHFFFAOYAE] [| tert-butyl isocyanide] [|InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3] InChIKey: [|FAGLEPBREOXSAC]-[|UHFFFAOYAL] [|crotonic acid] [|InChI=1/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2] InChIKey: [|LDHQCZJRKDOVOX]-[|NSCUHMNNBH] [|benzylamine] [|InChI=1/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2] InChIKey: [|WGQKYBSKWIADBV]-[|UHFFFAOYAL]