Reaktion #56684

Reaktionsgleichung

acetic acid

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

sodium methylate methanol

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

→

title compound

Ausbeute 76.0%

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

Ausbeute 76.0%

Lösungsmittel

water

methanol

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   workup.ADDITIONwas added dropwise over 30 min
3. 3
   workup.STIRRINGThe mixture was stirred at 0° C. for 1 hr
4. 4
   workup.ADDITIONwas added dropwise over 30 min
5. 5
   workup.STIRRINGThe mixture was stirred at 0° C. for 2 hr
6. 6
   Filtrationthe precipitated crystals were collected by filtration
7. 7
   WaschenThe obtained crystals were washed with methanol (1 L×2)
8. 8
   Sonstigedried in vacuo

Vorschrift

4-(4-Pyridyl)-1,3-thiazole-2-thiol (225 g, 1.16 mol) was suspended in tetrahydrofuran (1.5 L) and 28% sodium methylate-methanol solution (235 g, 1.22 mol) was added dropwise at 25° C. over 10 min. The mixture was stirred for 1 hr. The reaction mixture was ice-cooled and benzhydryl 7β-[(phenylacetyl)amino]-3-[(methylsulfonyl)oxy]-3-cephem-4-carboxylate (479 g, 0.83 mol) dissolved in tetrahydrofuran (3.5 L) was added dropwise over 30 min. The mixture was stirred at 0° C. for 1 hr and a mixture of acetic acid (50 mL), methanol (5 L) and water (7 L) was added dropwise over 30 min. The mixture was stirred at 0° C. for 2 hr, and the precipitated crystals were collected by filtration. The obtained crystals were washed with methanol (1 L×2) and dried in vacuo to give the title compound (438 g, 0.63 mol). yield: 76%.

Quelle