Methanesulfonyl chloride → HCID 53765200, compound

Participants

Reaction Conditions

Reaction Steps

Thionicotinamide (0.28 g) and pyridine (0.16 g) are added to a solution of the syn isomer of 2-benzhydryloxycarbonyl-3-(1-bromo-2-oxoethyl)-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (mixture of the two diastereoisomers) (1.66 g) in tetrahydrofuran (20 cc) and the mixture is heated at 50° C. for 90 minutes. The reaction mixture is subsequently cooled to 0° C. and then treated successively with methanesulphonyl chloride (0.23 g) and triethylamine (0.56 cc). After 30 minutes at 0° C., the reaction mixture is poured into a mixture of a saturated solution of sodium bicarbonate (200 cc) and ethyl acetate (100 cc); the organic phase is decanted, washed with distilled water (150 cc) and with a saturated solution of sodium chloride (150 cc) and then dried over magnesium sulphate. The residue obtained after evaporation of the solvent to dryness under reduced pressure (4 kPa) at 40° C. is chromatographed on a column (height: 30 cm, diameter: 1.5 cm) containing silica gel (0.04-0.06 mm), elution being carried out under a pressure of 0.5 bar (50 kPa) with a mixture of cyclohexane and ethyl acetate (30/70 by volume) and 50 cc fractions being collected. Fractions 18 to 26 are combined and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C. to give the syn isomer of 2-benzhydryloxycarbonyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetamido]-8-oxo-3-[2-(pyridin-3-yl)-thiazol-5-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene (0.18 g) in the form of a beige powder.

Provenance & Evidence