Triethylamine → 7-Bromo-heptanoic acid benzyloxyamide

Participants

Reaction Steps

In an ice bath, 2.4 ml triethylamine was added to a suspension of 2.7 g (17 mmol) O-benzylhydroxylamine hydrochloride in 100 ml dichloromethane. 3.6 g (17 mmol)7-bromo heptanoic acid was added, followed by 5.3 g (21 mmol) bis-(2-oxo-3-oxazolidinyl)-phosphorylchloride Stirring was continued at ambient temperature for 18 h. The solution was extracted twice with 150 ml each of 1M aqueous hydrochloric acid and twice with 150 ml each of 1M aqueous sodium bicarbonate. The organic solvent was removed i. vac. and the residue was purified by column chromatography (silica gel; ethyl acetate: heptane 1:1) to give 1.55 g (30%) of 7-bromo-heptanoic acid benzyloxy-amide as a colorless oil. MS: 314 (M+H+).

Provenance & Evidence