Exp184

=Objective= To synthesize a Ugi Product following the EXPLAN005 with phenanthrene-9-carboxaldehyde, cyclohexylamine, mandelic acid and t-butyl isocyanide. The compound will contribute towards a library for Falcipain2 inhibitors. This compounds was ranked 49 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 was conducted to obtain more data on the solubility of these starting materials in various solvents. =Procedure= As described in Explan005 This reaction used [|Phenanthrene-9-carboxaldehyde], [|cyclohexylamine], [|t-butylisocyanide] and [|Furoic acid]. [|HNMR]
 * Phenanthrene-9-Carboxaldehyde** (solid from Sigma-Aldrich)

This experiment is Ranked 49. It is a repeat of Exp 183 in three different solvents: ethanol, acetonitrile, and dichloromethane. Exp184-1 is in ethanol, Exp184-2 is in acetonitrile, and Exp184-3 is in dichloromethane.

carboxaldehyde || cyclohexylamine || Mandelic acid || t-butylisocyanide || Reagents Insoluble || carboxaldehyde || cyclohexylamine || Mandelic acid || t-butylisocyanide || Reagents Insoluble || carboxaldehyde || cyclohexylamine || Mandelic acid || t-butylisocyanide || Reagents Insoluble || (density=0.867g/ml) || 0.5mmol, 76.075 mg || 0.5mmol, 56.5uL (density=0.735g/ml) ||  ||
 * ID/ Lib Rank || Solvent || Aldehyde || Amine || Carboxylic Acid || Isocyanide || Ppt Yes/No ||
 * 184-1/49 || ethanol || Phenanthrene-9-
 * 184-2/49 || acetonitrile || Phenanthrene-9-
 * 184-3/49 || dichloromethane || Phenanthrene-9-
 * Quantity || 1000uL || 0.5mmol, 103.1mg || 0.5mmol, 57.2uL

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

=Results= Photos taken directly after all the components were charged and vortexed.
 * **184-1 A** || **184-2 A** || **184-3 A** ||
 * [[image:Exp184-1.JPG width="97" height="73" link="http://usefulchem.wikispaces.com/space/showimage/Exp184-1.JPG"]] || [[image:Exp184-2.JPG width="95" height="77" link="http://usefulchem.wikispaces.com/space/showimage/Exp184-2.JPG"]] || [[image:Exp184-3.JPG width="99" height="75" link="http://usefulchem.wikispaces.com/space/showimage/Exp184-3.JPG"]] ||

=Discussion= //**Some of the materials were soluble - discuss this. Also your acid might not have been the best choice as a trial run -why?**//

=Conclusion= The starting materials are insoluble in each solvent.

=Log=

2008-05-01
15:33- Charged vial 184-1 with 1000 ul of ethanol. 15:35- Charged vial 184-2 with 1000 ul of acetonitrile. 15:39- Charged vial 184-3 with 1000 ul of dichloromethane. 15:44- Weighed out the Phenanthrene-9-carboxaldehyde and mandelic acid for each of the three samples. 15:55- Added the cyclohexylamine to the vials. 15:59- Vortexed each vial 15 seconds each. Each sample was clear. 16:02- Added the phenanthrene-9-carboxaldehyde to each vial. 16:04- Vortexed vials for 3 minutes each. No clear solutions were obtained for Exp184-1 and Exp184-2. Vial Exp184-3 was clear. 16:14- Added the mandelic acid to each vial. 16:17- Vortexed vial 3 min. No clear solution was obtained. 16:27- Added the t-butyl isocyanide to each vial. 16:30- Vortexed 2 minutes each. No clear solutions were obtained. 16:38- Photos were taken of the vials **184-1 A**, **184-2 A**, and **184-3 A**.

=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] [|Mandelic acid] [|InChI=1/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1] InChIKey [|IWYDHOAUDWTVEP]-[|UHFFFAOYAD] [|cyclohexylamine][|InChI=1/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2]InChIKey[|IFYLVUHLOOCYBG]-[|UHFFFAOYAD]