Triphenylphosphine → Tert-butyl-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenylcarbamate

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 4-hydroxy-2-methylphenylcarbamate (3.0 g, 13.4 mmol), triphenylphosphine (3.53 g, 13.4 mmol), and [3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methanol (3.85 g, 13.4 mmol) in dichloromethane (40 mL) at 0° C. was treated with a solution of diisopropylazidodicarboxylate (2.65 mL, 13.4 mmol) in dichloromethane (10 mL) dropwise. The reaction was allowed to stir at 0° C. for 30 minutes, then warmed to ambient temperature for 1 h after which time the solvent was removed in vacuo. The resulting oil was chromatographed on silica gel eluting with 20% ethyl acetate/hexanes. Yield=4.34 g (66%) of tert-butyl 4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenylcarbamate.

Provenance & Evidence