Triethylamine → HCID 44511926, compound

Participants

Reaction Steps

Under an atmosphere of Argon, 2-tert-butoxycarbonylamino-4-chloro-5-fluoro-benzoic acid tert-butyl ester (200 mg) and 4-phenoxy-benzoyl chloride ([1623-95-6], 269 mg) were dissolved in THF (5 mL). Triethylamine (0.24 ml) was added, and the mixture was heated to reflux overnight. The solvent was evaporated, and the residue was purified by column chromatography (silica gel/methanol/dichloromethane). The eluate, which contained two UV-absorbing components, was evaporated, and the residue was dissolved in a mixture of dichloromethane (0.5 ml) and trifluoroacetic acid (0.5 ml). After 2 h, the volatiles were evaporated, and the title compound (9 mg, 0.4%) was isolated from the mixture by preparative, reversed-phase HPLC (Agilent Zorbax XdB C18 column, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 4.5 min, flow rate 30 ml/min). MS: m/e=384.1 [M+H+].

Provenance & Evidence