m-Chloroperbenzoic acid → (4-methoxyphenyl)methyl (5S,6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-5,8-dioxo-3-[(2S)-oxolan-2-yl]-5lambda4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

4-Methoxybenzyl (6R,7R)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-[(S)-tetrahydrofuran-2-yl)ceph-3-em-4-carboxylate (see example 7) (250 mg, 0.44 mmol) in ethyl acetate (25 ml) was stirred in an ice bath and a solution of m-chloroperbenzoic acid (75 mg, 0.44 mmol) in ethyl acetate (5 ml) was added. After 10 min the reaction mixture was washed with dilute aqueous sodium hydrogen carbonate then water followed by drying (magnesium sulphate) and evaporation under reduced pressure. The residue was chromatographed on silica gel eluting with acetone/ethyl acetate mixtures to give the title compound as a white solid (179 mg, 69%); νmax (CHCl3) 1800, 1730, 1680 and 1610 cm -1 ; δH (CDCl3) 1.48-1.64 (1 H,m), 1.89-2.00 (2 H,m), 2.33-2.47 (1 H,m), 3.29 and 3.75 (2 H, ABq, J 19 Hz), 3.82 (3 H,s), 3.84-3.96 (2 H,m), 4.09 (3 H,s), 5.06 (1 H,dd, J 7, 9 Hz), 5.22 (2 H,s), 5.55-5.8 (1 H, br s, exch), 6.16 (1 H,dd, J 4.5, 10 Hz), 6.91 (2 H,d, J 7,9 Hz), 6.98 (1 H,s), 7.35 (2 H,d, J 9 Hz) and 7.55-7.65 (1 H,br, exch). (Mass spectrum: +ve ion (thioglycerol) MH+ (590)].

1. washAfter 10 min the reaction mixture was washed with dilute aqueous sodium hydrogen carbonate
2. customby drying
3. custom(magnesium sulphate) and evaporation under reduced pressure
4. customThe residue was chromatographed on silica gel eluting with acetone/ethyl acetate

ORD record

ord-9a59c41ad2fd4d57997345979b266f07

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06001997