1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (+)-(2S)-2-(Methylpropan-2-yl)oxycarbonylamino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide

Participants

Reaction Steps

A mixture of N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine (100 mg), Boc-L-alanine (70 mg), EDAC (100 mg), and DMAP (60 mg) in DCM (8 ml) was stirred overnight. The reaction mixture was partitioned between EtOAc and water (8 ml each×3). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purificatied by flash chromatography on silica (33% EtOAc in hexane), which yielded (+)-(2S)-2-(Methylpropan-2-yl)oxycarbonylamino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide as a resin: MS (m+1)=441.1. The chiral integrity of this compound was not examined.

Provenance & Evidence