Acetic Acid → HCID 14230819, compound

Participants

Reaction Steps

To a solution of benzyl [3-phenoxyacetamido-4-(2,2,2-trichloroethoxycarbonylthio)-2-oxo-1-azetidinyl]glyoxylate (7.5 g.) and acetic acid (2.28 ml.) in tetrahydrofuran (30 ml.) was added portionwise sodium borohydride (480 mg.) over a period of half an hour at 0° C. After stirring for 10 minutes, the reaction mixture was diluted with methylene chloride (50 ml.), poured into a mixture of sodium bicarbonate (6.0 g.) in water (80 ml.) and a saturated aqueous solution of sodium chloride (20 ml.), and then extracted with methylene chloride (100 ml.). The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and then filtered through a pad of Celite. Removal of the solvent gave an amorphous solid (7.60 g.) of benzyl 2-[3-phenoxyacetamido-4-(2,2,2-trichloroethoxycarbonylthio)-2-oxo-1-azetidinyl]-2-hydroxyacetate.

Provenance & Evidence