Acetyl chloride → HCID 86741566, compound

Participants

Reaction Conditions

Reaction Steps

(S)-3-[[(Phenylmethoxy)carbonyl]amino]-2-azetidinone (2.2 g) was suspended in 100 ml of anhydrous tetrahydrofuran and cooled to -50° C. with stirring. Chlorosulfonylisocyanate (1.56 g) was added and the temperature was maintained at 0° C. for 30 minutes. After this time 3.51 g of heptamethyl disilazane was added and stirring at room temperature was continued overnight. Acetyl chloride (3.14 g) was added and the solution was stirred for an additional 48 hours. The solvent was removed in vacuo, and the residue dissolved in ethyl acetate and extracted twice with 50 ml portions of water. The aqueous layer was discarded and the ethyl acetate solution was dried with Na2SO4 and evaporated to dryness. The residue was dissolved in acetone/water (9:1), the pH adjusted to 6.5 with 1N KOH and the acetone removed in vacuo. The remaining aqueous solution was freeze-dried. The resulting crude compound (1.9 g) was purified by HP-20 chromatography, yielding 1.03 g of product.

Provenance & Evidence