Acetone → benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of 1.00 g of (3S)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, 8-hydroxyquinolinium salt in 75 ml of anhydrous ethanol under nitrogen was placed in a 95° C. oil bath. The mixture was refluxed for 20 minutes, then cooled to 20° C. with an ice water bath. The solvent was removed on the rotary evaporator (bath temperature ≥30° C.). The residue was taken up in 10 ml of water and 80 ml of ethyl acetate. About 600 mg of MgSO4 was added followed by 570 mg of sodium bicarbonate. The mixture was stirred to effect solution. The organic layer was separated, washed with 5 ml of water, and dried over MgSO4. The solvent was evaporated to afford a white solid, which was tranferred to a 25 ml flask with acetone. The acetone was removed in vacuo and the solid residue was suspended in ca. 5 ml of ethyl acetate. Ether (ca. 6 ml) was added and the mixture was stored for 60 minutes at 0° C. The solid was isolate by filtration, washed with ether, and dried in vacuo to afford 392 mg of the title compound as a white solid.

Provenance & Evidence