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

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Reaction Steps

Triethylamine (58.8 mg, 0.581 mmol) was added to a 0° C. solution of tert-butyl (4S,7S,10aS)-7-carbamoyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (57 mg, 0.17 mmol) in DCM (1.2 mL). TFAA (52.3 mg, 0.249 mmol) was then slowly added to the reaction. The ice bath was removed and the reaction mixture was left to stir at rt for 1 hr. The reaction was diluted with DCM (2 mL) and quenched by the addition of aqueous 10% Na2CO3 (2 mL). The aqueous phase was isolated and extracted with DCM (2 mL). All organic phases were combined, dried over MgSO4, filtered and concentrated. The crude product was purified using silica gel chromatography (ISCO system) eluting with a gradient of 0-100% EtOAc/Hex to give tert-butyl (4S,7S,10aS)-7-cyano-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (36 mg, 0.11 mmol, 67% yield) as a light yellow solid. Anal. Calcd. for C15H23N3O3S m/z 325.4. found: 326.3 (M+H)+.

Provenance & Evidence