Trimethyl orthoformate → tert-butyl (4S,7S,10aS)-7-(1,3,4-oxadiazol-2-yl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added tert-butyl (4S,7S,10aS)-7-(hydrazinecarbonyl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (0.13 g, 0.35 mmol) and trimethoxymethane (2.50 mL, 22.9 mmol). The reaction was heated at 70° C. for 5 hr. and then at 95° C. for 18 hr. The reaction was concentrated. The residue was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-60% EtOAc/Hex to give tert-butyl (4S,7S,10aS)-7-(1,3,4-oxadiazol-2-yl)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (94 mg, 0.26 mmol, 73% yield) as a white solid. Anal. Calcd. for C16H24N4O4S m/z 368.4. found: 369.1 (M+H)+.

Provenance & Evidence