1-Hydroxybenzotriazole → HCID 86654321, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.11 g (4.96 mmol) of (+/−)-(2S,3S)-3-(2-amino-6-(benzyloxy)phenylthio)-2-hydroxy-3-(4-methoxyphenyl)propanoic acid in 25 mL of DMF was added 1.24 g (6.47 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 871 mg (6.45 mmol) of 1-hydroxybenzotriazole. The solution was stirred at 22° C. for 16 hours, and a solution of 7:3 ethyl acetate/methanol was added to the reaction. The organic layer was washed with 1 N HCl (2×) and then with a 1:1 mixture of satd. NaHCO3 and brine (2×). The organic layer was dried (Na2SO4) and evaporated. The residue was purified by flash chromatography on silica gel, eluting first with hexane then gradually increasing to 40% ethyl acetate/hexane to give (+/−)-(2S,3S)-9-(benzyloxy)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]thiazepin-4(5H)-one.

Provenance & Evidence