Methanol → HCID 10646910, compound

Participants

Reaction Steps

To a solution of 500 mg (1.61 mmoles) of cis-3-carboxyvinyl-4-benzyloxyphenylacetic acid in 30 ml of CH2Cl2 is added 522 mg (3.22 mmoles) of 1,1'-carbonyldiimidazole (CDI). After 30 minutes, 234 ml (1.61 mmoles) of N-methyl-N-phenethylamine is added. After 18 hours a catalytic amount of 4-dimethylaminopyridine and 5 ml of methanol are added. After stirring for 21/2 hours, the reaction mixture is concentrated down in vacuo, taken up in ethyl acetate, washed with 1N NaOH, 1N HCl, H2O (2 times), brine (2 times), dried with MgSO4, filtered and concentrated in vacuo. The crude product is purified by flash chromatography to yield trans-N-methyl-N-phenethyl-2-[4-benzyloxy-3-(2-carbomethoxyvinyl)phenyl]acetamide. NMR confirms this structure which is used directly in the next step.

Provenance & Evidence