tert-Butanol → HCID 90203445, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[4-(4-methoxy-benzyloxy)-phenyl]-isoxazole-4-carboxylic acid (16.16 g, 49.7 mmol) in DMF (50 mL) was added diphenylphosphoryl azide (15.04 g, 54.6 mmol) and triethylamine (7.62 mL, 54.64 mmol). The orange solution was heated to 50° C. and allowed to stir 3.5 h. At this time, tert-butanol (100 mL) was added and the reaction mixture was heated to 84° C. for 14 h after which it was cooled to rt. Concentration in vacuo gave a dark orange oil from which {3-[4-(4-methoxy-benzyloxy)-phenyl]-isoxazol-4-yl}-carbamic acid tert-butyl ester (3.01 g, 15%) was isolated by chromatography (25-50% ethyl acetate in hexane).

Provenance & Evidence