Triethylamine → 1-(3-Benzyloxy-4-methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid benzyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 13 g of 5-oxo-2-pyrrolidinepropanoic acid benzyl ester in 250 ml of tetrahydrofuran is treated with 14.0 g of 3-benzyloxy-4-methoxybenzoyl chloride. The mixture is heated to 55° C. and a solution of 5.5 g of triethylamine in 400 ml of tetrahydrofuran is added dropwise over a two hour period. The mixture is stirred and heated at 55° C. for 16 hours. The warm mixture is filtered through filter aid to remove triethylamine hydrochloride and concentrated at reduced pressure. Chromatography over silica using a Waters Prep 500 HPLC apparatus yields 1-(3-benzyloxy-4-methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid benzyl ester with mp 92°-95° C. after concentration and crystallization.

Provenance & Evidence