Acetic Acid → Diphenylmethyl (6R,7R)-8-oxo-7-((phenylacetyl)amino)-3-((4-(pyridin-4-yl)-1,3-thiazol-2-yl)thio)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

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Reaction Conditions

Reaction Steps

Benzhydryl 7β-[(phenylacetyl)amino]-3-[(methylsulfonyl)oxy]-3-cephem-4-carboxylate (900 g, 1.56 mol) was dissolved in tetrahydrofuran (3.6 L) and cooled to −3° C. While maintaining the same temperature, 28% sodium methylate-methanol solution (360 g, 1.87 mol) of 4-(4-pyridyl)-1,3-thiazole-2-thiol (362.5 g, 1.87 mol) obtained in the same manner as in Reference Example 29, and tetrahydrofuran (720 mL) solution were added. The mixture was stirred for 1.5 hr. Acetic acid (18.7 g) was added and after stirring for 30 min, methanol (9 L) and water (5.4 L) were added. The mixture was stirred for 2 hr. The precipitated crystals were collected by filtration, washed with methanol (16 L) and dried in vacuo. yield: 884 g (84%)

Provenance & Evidence