Dichloromethane → HCID 18609333, compound

Participants

Reaction Conditions

Reaction Steps

To the flask containing (±)-(Z)-2-[[[1-(2-amino-4-thiazolyl)-2-[[4,4-dimethyl-2-oxo-1-(sulfooxy)-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-propenoic acid, diphenylmethyl ester was added methylene chloride (10 ml) and anisole (10 ml). After cooling to -5° C., trifluoroacetic acid (8 ml) was added and the reaction mixture was stirred at -5 to 0° C. under argon for 45 minutes. Toluene was added, and the reaction mixture was evaporated to a residue. Water and hexane were added to the residue and the layers were separated. The aqueous layer was adjusted to pH 2.5 with 10% potassium bicarbonate. An HP20 column was run eluting first with water and then an acetone/water gradient. The appropriate fractions were combined and lyophilized to give the title compound as a white solid. 1H-NMR (1:1 D2O/CD3CN) δ1.57 (s, 3H); 1.75 (s, 3H); 5.09 (s, 1H); 5.75 (d, J =2.3 Hz, 1H); 5.86 (d, J2.3 Hz, lH); 7.42 (s, 1H).

Provenance & Evidence