Triethylamine → (3S)-3-[[(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-N-[(5-methyl-1,2-thiazol-3-yl)sulfamoyl]-2-oxoazetidine-1-carboxamide

Participants

Reaction Steps

A solution of 436 mg (4.32 mmol) of triethylamine in 3.2 mL of dry DMF was cooled to -8° C. and 502 mg (1.2 mmol) of (S)-3-amino-N-[[(5-methyl-3-isothiazolyl)amino]sulfonyl]-2-oxo-1-azetidinecarboxamide trifluoroacetic acid salt was added. To the resulting solution was added dropwise a solution of 520 mg (1.2 mmol) of (Z)-[2-(chloroacetyl)amino-4-thiazolyl](methoxyimino)acetyl chloride hydrochloride in 4 mL of chloroform. The mixture was stirred cold for 15 minutes and at room temperature for three hours before concentrating under reduced pressure. Methylene chloride was added to the residue, and evaporation under reduced pressure was repeated. The residue was taken up in ethyl acetate and water, and the mixture adjusted to pH3 with N hydrochloric acid. The organic phase was washed with brine, dried (Na2SO4), decolorized with charcoal, and concentrated under reduced pressure to obtain 420 mg of the title compound.

Provenance & Evidence