Sodium Acetate → HCID 68618323, compound

Participants

Reaction Conditions

Reaction Steps

To 14-tert-butoxycarbonylamino-18-(4-fluoro-1,3-dihydro-isoindole-2-carbonyloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid methyl ester (392 mg, 0.61) in DME (3 mL) and water (1 mL) was added tosyl hydrazide (682 mg, 3.66 mmol) and sodium acetate (600 mg, 7.32 mmol). The reaction was heated to 95° C. and allowed to stir 1 hour. The reaction was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated. The crude product was purified by column chromatography on silica (40→60% EtOAc/Hexanes) to provide 14-tert-butoxycarbonylamino-18-(4-fluoro-1,3-dihydro-isoindole-2-carbonyloxy)-2,15-dioxo-3,16-diaza-tricyclo[14.3.0.04,6]nonadecane-4-carboxylic acid methyl ester (319 mg, 81% yield). LCMS found 644.8 [M+H]+.

Provenance & Evidence