Acetic Anhydride → HCID 59516076, compound

Participants

Reaction Conditions

Reaction Steps

t-Butyl cyanoacetate (600 mg, 4.25 mmol) was dissolved in triethyl orthoformate (1.06 ml, 6.38 mmol), acetic anhydride (0.40 ml, 4.25 mmol) was added and the mixture heated to 125° C. for 2 hours. The solution was evaporated to leave a yellow oil. This oil was redissolved in ethanol (5 ml) and treated with 4-Hydrazinomethyl-benzoic acid methyl ester hydrochloride (Intermediate#52) (230 mg, 1.06 mmol) and DIPEA (184 μl, 1.06 mmol). The resulting mixture was heated to reflux for 2 h and then cooled to ambient temperature and evaporated to leave a brown oil. This oil was dissolved in ethyl acetate (50 mL), washed with water (2×20 mL) and brine (20 mL) then dried (MgSO4), filtered and evaporated. The residue was chromatographed (40 g silica EtOAc/Hexane 0-50%) to yield the title compound as a yellow solid (214 mg, 43%).

Provenance & Evidence