Boron trifluoride etherate → N,N,N',N'-tetramethyl 3,3'-(((3-(2-(4-(1-methylethyl)-2-thiazolyl)ethenyl)phenyl)methylene)bis(thio))-bispropanamide

Participants

Reaction Steps

To a solution of the aldehyde of Step 1 (430 mg), methyl 3-mercaptopropanoate (190 μL, 1 equiv.) and N,N-dimethyl 3-mercaptopropanamide (223 mg, 1 equiv.) in CH2Cl2 (10 mL), BF3.Et2O (620 μL, 3 equiv.) is added slowly and the mixture is stirred 1.5 hours. The reaction is quenched with 25% aqueous NH4OAc at 0° C. The products are extracted with EtOAc and separated by flash chromatography on silica using a gradient of EtOAc:toluene (from 10:90 to 40:60) and acetone:toluene 1:1. Three products are obtained: first, dimethyl 3,3'(((3-(2-(4-(1-methylethyl)-2-thiazolyl)ethenyl)phenyl)methylene)-bis (thio))bispropanoate; second, methyl 3-((1-((3-dimethylamino-3-oxopropyl)thio)-1-(3-(2-(4-(1-methyl-ethyl)-2-thiazolyl)ethenyl)phenyl)methyl)thio)-propanoate; and third, the title compound.

Provenance & Evidence