1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-N-(1-(3-chlorophenyl)ethyl)-4-methoxy-3-(morpholinosulfonyl)benzamide

Participants

Reaction Steps

To a solution of 4-methoxy-3-(morpholinosulfonyl)benzoic acid 42 (0.824 g, 2.73 mmol) in DMF (6 mL) was added EDCI (0.686 g, 3.58 mmol) and HOBT (0.536 g, 3.50 mmol), the solution was stirred for 30 min and (R)-1-(3-chlorophenyl)ethanamine (0.673 g, 4.32 mmol) was added. The reaction mixture was stirred at room temperature for 16 h and diluted with EtOAc and water. The organic phase was washed with water (2×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 60% to 100% EtOAc in hexanes) gave (R)—N-(1-(3-chlorophenyl)ethyl)-4-methoxy-3-(morpholinosulfonyl)benzamide 43 (1.14 g, 95.0% yield) as a white solid. Mass spectrum: calculated for C20H23ClN2O5S 438.1. found 439.1 (M++1).

Provenance & Evidence