Reaktion #56686

Reaktionsgleichung

Acetic acid

sodium methylate methanol

4-(4-pyridyl)-1,3-thiazole-2-thiol

Benzhydryl 7β-[(phenylacetyl)amino]-3-[(methylsulfonyl)oxy]-3-cephem-4-carboxylate

→

benzhydryl 7β-[(phenylacetyl)amino]-3-[4-(4-pyridyl)-2-thiazolylthio]-3-cephem-4-carboxylate

Lösungsmittel

tetrahydrofuran

water

methanol

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGafter stirring for 30 min
3. 3
   workup.STIRRINGThe mixture was stirred for 2 hr
4. 4
   FiltrationThe precipitated crystals were collected by filtration
5. 5
   Waschenwashed with methanol (16 L)
6. 6
   Sonstigedried in vacuo

Vorschrift

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%)

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