Dimethylformamide → HCID 131736354, compound

Participants

Reaction Steps

NaH (60% in mineral oil, 16 mg, 0.40 mmol, Eq: 1.50) was added to a solution of tert-butyl (S)-1-(4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (100 mg, 0.26 mmol, Eq: 1.00) in DMF at RT. After 5 min. benzyl bromide (35 μL, 0.29 mmol, Eq: 1.10) was added, the mixture was stirred for 35 min., diluted with 1 N HCl and extracted with EtOAc. The organic extracts were washed with sat. NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography to afford tert-butyl (S)-1-(5-benzyl-4-oxo-2,3,4,5-tetrahydro-benzo[1)][1,4]thiazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (96 mg, 77%).

Provenance & Evidence