Water → HCID 14010105, compound

Participants

Reaction Conditions

Reaction Steps

A solution of chlorosulfonic acid (12.27 g, 0.105 mole) in 210 ml of dichloromethane at -40° C. under argon was treated with 20.5 g (0.26 mole) of pyridine dropwise over 10 minutes. The mixture is stirred for 10 more minutes at 0° C. and 10 minutes at 25° C. A slurry of (±)-3-[(t-butyloxycarbonyl)amino]-1-hydroxy-4,4-dimethyl-2-azetidinone in 20 ml of dichloromethane was added and the mixture stirred at 25° C. for 3.5 hours. The nearly homogenous solution was then treated with 250 ml of water and 17 g (0.05 mole) of tetrabutylammonium hydrogen sulfate. The mixture was mixed well and the organic layer separated and dried over sodium sulfate. Evaporation in vacuo gave a foam, which was purified further by dissolution in ethyl acetate, removing insolubles, and evaporation to the title compound as a foam, 30 g.

Provenance & Evidence