Acetyl chloride → (S)-N-[(2S,3S)-1-(4-acetyl-benzoyl)-5-(5-bromo-2-methoxy-naphthalen-1-ylmethyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-2-methylamino-propionamide hydrochloride

Participants

Reaction Steps

Acetyl chloride (0.5 ml, 7.03 mmol) was added dropwise to a solution of {(S)-1-[(2S,3S)-1-(4-acetyl-benzoyl)-5-(5-bromo-2-methoxy-naphthalen-1-ylmethyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (40 mg, 0.52 mmol) in methanol at 0° C. and the reaction was allowed to warm to ambient temperature and stir for 2 h. The reaction was concentrated in vacuo and the residue was triturated with diethyl ether, filtered and dried to give (S)-N-[(2S,3S)-1-(4-acetyl-benzoyl)-5-(5-bromo-2-methoxy-naphthalen-1-ylmethyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl]-2-methylamino-propionamide hydrochloride (30 mg, 82%). LR-MS [M+H+]672, 673

Provenance & Evidence