(6R,7R)-7-[[(2Z)-2-methoxyimino-2-[5-[(2-methylpropan-2-yl)oxycarbonylamino]-1,2,4-thiadiazol-3-yl]acetyl]amino]-8-oxo-3-(3-oxobutanoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid → (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(3-oxobutanoyloxymethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Participants

Reaction Steps

To 50 ml of trifluoroacetic acid is added 13 g of 7β-[2-(5-tert-butoxycarbonylamino-1,2,4-thiadiazol-3-yl)-2(Z)-methoxyiminoacetamido]-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid with stirring under ice-cooling. The cooling bath is removed and stirring is continued for 30 minutes. Trifluoroacetic acid is evaporated off under reduced pressure. To the residue is added 100 ml of ethyl acetate and the ethyl acetate is removed under reduced pressure. To the residue is added 100 ml of diethyl ether. Trituration and filtration of the resulting powder give 10 g of the above-identified compound.

Provenance & Evidence