Exp178

== =Objective= To synthesize a [|Ugi Product] following the EXPLAN005. The compound will contribute towards a library for Falcipain2 inhibitors. This compounds was ranked 29 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]. This experiment is a repeat of Experiment 176 to make sure that I also got a positive result, because every other experiment I have attempted failed to dissolve/ form a precipitate. =Procedure= As described in Explan005 This reaction used [|Phenanthrene-9-carboxaldehyde], [|furfurylamine], [|n-butyl isocyanide] and [|phenylacetic acid]. [|HNMR] carboxaldehyde || furfurylamine || Phenylacetic acid || n-butylisocyanide || Yes || (density=1.099g/ml) || 0.5mmol, 68.1mg || 0.5mmol, 52.3uL (density=0.795g/ml) ||  ||
 * Phenanthrene-9-Carboxaldehyde** (solid from Sigma-Aldrich)
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 178/29 || Methanol || Phenanthrene-9-
 * Quantity || 1000uL || 0.5mmol, 103.1mg || 0.5mmol, 44.2uL

Density information found on the Ugi Chemicals Page in Left Navigation Bar.

=Results= Photos taken directly after all the components were charged and vortexed.

All results are recorded Master Table and Workflow Tables.

=Discussion= This experiment demonstrated that I could successfully produce a precipitate from a control Ugi reaction that is known to have a positive result. This also supports my theory that the solubility of phenanthrene-9-carboxaldehyde is dependent on the amine. Furfurylamine has an oxygen in the ring, which increases its reactivity and allows it to participate in hydrogen bonding, thus making it soluble in methanol.

=Conclusion= Experiment was successful with the formation of a precipitate. Experiment proved that I am completing experiments correctly. A further discussion of the apparent amine selective solubility of phenanthrene-9-carboxaldehyde is presented here.

=Log=

2008-02-28
15:44- Weighed out the Phenanthrene-9-carboxaldehyde. 15:50- Weighed out the phenylacetic acid. 15:55- Charged a vial with 1000 ul of methanol. 16:15- Added the furfurylamine to the vial. 16:16 Vortexed vial 1 min 16:17- Added the phenanthrene-9-carboxaldehyde. 1618-Vortexed vial 1 min 16:19- Added the phenylacetic acid. 16:20-Vortexed vial 1 min 16:21- Added the n-butyl isocyanide. 16:22-Vortexed 13min. 16:35-A clear solution was obtained 16:35- A photo was taken (178A) after the dissolution of all the reagents

2008-02-28
13:05 A photo was taken showing the formation of a precipitate (178B)

=Tags= [|furfurylamine] [|InChI=1/C5H7NO/c6-4-5-2-1-3-7-5/h1-3H,4,6H2] InChIKey: [|DDRPCXLAQZKBJP]-[|UHFFFAOYAX] [|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] [|QECIGCMPORCORE]-[|UHFFFAOYAE] [|phenylacetic acid] [|InChI=1/C8H8O2/c1-7(9)10-8-5-3-2-4-6-8/h2-6H,1H3] [|WLJVXDMOQOGPHL]-[|UHFFFAOYAR] [|n-butyl isocyanide] [| InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3] InChIKey: [|FSBLVBBRXSCOKU]-[|UHFFFAOYAR] [|Ugi Product] [|InChI=1/C3 ​3H32N2O3/c​1-2-3-19-3​4-33(37)32​(30-22-25-​14-7-8-16-​27(25)28-1​ 7-9-10-18-​29(28)30)3​5(23-26-15​-11-20-38-​26)31(36)2​1-24-12-5-​ 4-6-13-24/​h4-18,20,2​2,32H,2-3,​19,21,23H2​,1H3,(H,34​,37)] InChIKey:[| RGGYLRDGJAJICY]-[|UHFFFAOYAH]