Triethylamine → N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-phenylglycine methyl ester

Participants

Reaction Steps

To a solution of 3-(4,5,7-trifluorobenzothiazol-2-yl)propionic acid (522 mg, 2 mmol) obtained in Example 3-i) in a mixture of toluene (5 ml) and N,N-dimethylformamide (DMF; 1 ml) was added thionyl chloride (357 mg, 3 mmol) and the mixture was stirred for 1 hour at room temperature. To the ice cold reaction mixture was N-phenylglycine methyl ester hydrochloride (403 mg, 2 mmol) and triethylamine (400 mg, 4 mmol) and the mixture was stirred for 2 hours. The reaction mixture was diluted with water and then extracted with ethyl acetate. The organic layer was washed with water, then dried and evaporated to yield a residue, which was purified on a silica gel column to give N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-phenylglycine methyl ester (240 mg, 29%) as an oil.

Provenance & Evidence