Triethylamine → HCID 86734117, compound

Participants

Reaction Steps

To a cooled solution of α-tert.-butoxycarbonylaminophenylacetic acid (1.0 g) and triethylamine (405 mg) in tetrahydrofuran (16 ml), is added isobutylchloroformate (550 mg) at -10°C and the mixture is stirred for 10 minutes. To the solution is added a solution of 7β-amino-3β-chloro-3α-methylcepham-4α-carboxylic acid (870 mg), and triethylamine (405 mg) in a mixture of tetrahydrofuran and water (1:1; 15 ml), and the mixture is stirred for 1 hour at 5°C, and for 1 hour at room temperature. The reaction mixture is evaporated in vacuo to remove tetrahydrofuran, and the resultant solution is diluted with a mixture of water and ethyl acetate (3:1). The aqueous layer is separated, acidified to pH 3 with 10% hydrochloric acid, and extracted with ethyl acetate. The extract solution is washed with water, dried, and evaporated to give 7β-(α-tert.-butoxycarbonylaminophenylacetamido)-3β-chloro-3α-methylcepham-4α-carboxylic acid (1.5 g). Yield: 77%.

Provenance & Evidence