Sodium Chloride → HCID 10439229, compound

Participants

Reaction Steps

Under a stream of dry nitrogen, the flask was charged with 500 mg (0.65 mmol) of diphenylmethyl 2-[(3R, 4R)-4-[(benzothiazol-2-yl)dithio]-3-phenylacetamido-2-oxo-azetidin-1-yl]-3-fluorosulfonyloxy-2-butenoate (XVf) and 5.0 mL of dry THF. After stirring the solution for 15 min at 0°-5° C., 92.0 μL (0.65 mmol) of triethylamine was added dropwise. Stirring at 0°-5° C. under a blanket of dry nitrogen was continued for 2 h. The solution was diluted with THF (10 mL) and poured into an aqueous saturated NaCl solution (30 mL). The phases were separated and the organic phase was dried 15 min over anhydrous MgSO4, filtered and concentrated to a small volume (ca. 6 mL). The solution was added dropwise into 36 mL of hexanes with vigorous stirring. After 30 min, the solid was collected by suction filtration and dried in vacuo for 3 h at 22° C. to yield 387 mg (92%) of the title product as a beige powder.

Provenance & Evidence