Dichloromethane → N-((R)-methylphenylphosphinyl)-N-benzyl-D-leucine methyl ester

Participants

Reaction Conditions

Reaction Steps

Methylphenyl-phosphinic chloride (361 mg, 2.07 mmol) is dissolved in dichloromethane (2.5 mL) and then cooled to 0° C. To this is added a solution of N-benzyl D-alanine methyl ester (400 mg, 2.07 mmol) and N-methyl morpholine (0.51 mL, 4.6 mmol) in dichloromethane (2.5 mL). A catalytic amount of 4-dimethylaminopyridine is then added to the stirring mixture. The reaction is stirred for 16 hours at room temperature, washed with water and brine, dried over sodium sulfate, and concentrated. The crude product is purified by silica gel flash chromatography (100% ethyl acetate) to give N-((R)-methylphenylphosphinyl)-N-benzyl-D-leucine methyl ester as an oil.

Provenance & Evidence