Methyl acetoacetate → tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-{[4-(methoxycarbonyl)-5-methyl-1H-1,2,3-triazol-1-yl]methyl}-1,4-oxazepane-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (6S,7R)-6-(azidomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (200 mg) in DMSO (2 mL) were added potassium carbonate (276 mg) and methyl acetoacetate (0.08 mL) at room temperature, and the mixture was stirred at 80° C. overnight. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (149 mg).

Provenance & Evidence