Hydrogen Peroxide → Diphenylmethyl (4R, 6R, 7R)-3-(1,4-dihydroxybut-1-yl)-7-phenylacetamidoceph-2-em-4-carboxylate

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Reaction Steps

Borane-tetrahydrofuran complex (1M in tetrahydrofuran, 11.0 ml, 11.0 mmol) was added to diphenylmethyl (4R, 6R, 7R)-3-(1-hydroxybut-3-en-1-yl)-7-phenylacetamidoceph-2-em-4-carboxylate (S-diastereomer, 100 mg, 0.18 mmol) in tetrahydrofuran (2 ml) at 20° C. After 30 minutes water (1 ml) was added and the pH taken to within the range 7 to 8 with dilute aqueous sodium hydroxide. Hydrogen peroxide (30% in water, 0.15 ml, 1.35 mmol) was then added, and the pH maintained at 7 to 8 for 20 minutes, after which water and ethyl acetate were added. The organic layer was washed with brine, dried (MgSO4), and evaporated to give a residue which was purified by chromatography (50 to 100% ethyl acetate in hexane, silica gel) giving the S-diastereomer of the title compound identical to that obtained above (isomer P1), 35 mg (34%).

Provenance & Evidence