Trifluoroacetic acid → (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(isothiocyanatomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Participants

Reaction Steps

To a solution of 3-aminomethyl-7-[2-(2-aminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido]ceph-3-em-4-carboxylic acid (1.34 g.) in acetonitrile (100 ml.), water (30 ml.) and triethylamine (1.01 g.) at -15° was dropwise added thiophosgene (250 ul.). The mixture was stirred for 30 minutes at -15° and then the pH of the mixture was adjusted to 3-4 by addition of TFA. The solvent was evaporated and the residue purifed by HPLC using an aqueous ammonium carbonate buffer, pH 6-7/MeOH 70:30 v/v as eluant to give 7-[2-(2-aminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido]3-isothiocyanatomethylceph-3-em-4-carboxylic acid having the following nmr in solvent B:--3.56 (d, 1 H); 3.84 (d, 1 H); 4.08 (s, 3 H); 4.6 (d, 1 H); 4.84 (d, 1 H); 5.3 (d, 1 H); 5.96 (d, 1 H); 7.14 (s, 1 H).

Provenance & Evidence