Methanesulfonyl chloride → HCID 9915982, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid (0.108 g, 0.537 mmol) in DMF (2 ml) was cooled to -50° C. N,N-Diisopropylethylamine (0.103 ml, 0.59 mmol) followed by methanesulphonyl chloride (0.046 ml, 0.59 mmol) were added and the mixture was stirred at -50° C. for 30 min. A further quantity of N,N-diisopropylethylamine (0.086 ml, 0.493 mmol) was added and this mixture was added to a pre-cooled solution of pivaloyloxymethyl (6R,7R)-7-amino-3-[(S)-tetrahydrofuran-2-yl]ceph-3-em-4-carboxylate (0.185 g, 0.482 mmol) in DMF (2 ml) at 0° C. The resulting mixture was stirred at 0° C. for 40 min., then it was partitioned between ethyl acetate and water. The organic phase was washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by flash chromatography, then triturated with ether to give the title compound (0.193 g, 71%) as a white solid. The spectral data was identical with that obtained for Example 8.

Provenance & Evidence