Exp159

== =Objective= To synthesize a Ugi adduct from benzylamine, phenanthrene-9-carboxaldehyde, 4-chlorophenyl acetic acid and n-butyl isocyanide in methanol using Ugi 4CR following Explan005. The target compound was ranked 18 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) and benzylamine, phenanthrene-9-carboxaldehyde, 4-chlorophenyl acetic acid and n-butyl 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.

carboxaldehyde || benzylamine || 4-chlorophenyl acetic acid || n-butyl isocyanide || Aborted || (density=0.981g/ml) || 0.5mmol, 85.30 mg || 0.5mmol, 52.28 ul (density=0.795g/ml) ||  ||
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 159/18 || Methanol || Phenanthrene-9-
 * Quantity || 1000uL || 0.5 mmol, 103.12 mg || 0.5mmol, 54.6uL

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

=Results=

all components (159A)** || **One day after mixing all components (159B)** ||
 * **5 min after mixing
 * [[image:Exp159day1.JPG width="126" height="94" link="http://usefulchem.wikispaces.com/space/showimage/Exp159day1.JPG"]] || [[image:Exp159day2.JPG width="126" height="93" link="http://usefulchem.wikispaces.com/space/showimage/Exp159day2.JPG"]] ||


 * **(159C)** ||  ||
 * [[image:Exp159C.JPG width="137" height="102" link="http://usefulchem.wikispaces.com/space/showimage/Exp159C.JPG"]] ||  ||

=Discussion=

All results are recorded Master Table and Workflow Tables. =Conclusion=
 * [So it looks like you get a clear solution when the phenanthrene-9-carboxaldehyde is mixed with benzylamine in methanol JCB]**

After one day a precipitate was obtained but the solvent was evaporated without washing - aborted and to be repeated.

=Log=

2008-01-18
16:03- Started to weigh out the phenanthrene-9-carboxaldehyde. 16:09- Started to weigh out the 4-chlorophenyl acetic acid. 16:14- Charged a vial with 1 mL of methanol. 16:16- Added the benzylamine to the vial and vortexed for 15 seconds. A clear solution was obtained. 16:20- Added the phenanthrene-9-carboxaldehyde to the vial and vortexed for 5 minutes until a clear solution was obtained. 16:26- Added the 4-chlorophenyl acetic acid to the vial and vortexed for 15 seconds. A clear solution was obtained. 16:30- Added the n-butyl isocyanide to the vial and vortexed for 15 seconds. A clear solution was obtained. 16:33- Took a photo of the vial and left it to sit for 24 hours at room temperature.

16:38- Took a photo of the vial after one day. A most of the liquid in the vial precipitated into a solid.
 * 2008-01**-**19**

15:34- Vortexed the product in the vial for 15 seconds. No solvent was visible. 15:36- Added 500 ul of methanol to the vial and vortexed for 15 seconds. The solvent remained over the solid. 15:40- Sonicated the vial containing undissolved solid and methanol on top for 1 min, then vortexed it for 15 sec. At this time the solid packing at the bottom of the vial mixed well with the solvent and a pasty mixture covered the walls of the vial. 15:43- The vial was then emptied onto a clean watch glass. 15:45- The vial was rinsed with 250 ul of methanol, and then the contents were emptied onto a watch glass. 15:47- A photo was taken (159C) of the watch glass and empty vial. The methanol will evaporate so the product can be weighed.
 * 2008-02-08**

=Tags= [|benzylamine] [|InChI=1/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2] InChIKey: [|WGQKYBSKWIADBV]-[|UHFFFAOYAL] [|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] [|4-chlorophenyl acetic acid] [|InChI=1/C8H7ClO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H,10,11)] [|n-butyl isocyanide] [| InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3] InChIKey: [|FSBLVBBRXSCOKU]-[|UHFFFAOYAR]