反応 #56686

反応方程式

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

溶媒

tetrahydrofuran

water

methanol

tetrahydrofuran

反応条件

後処理

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
   ろ過The precipitated crystals were collected by filtration
5. 5
   洗浄washed with methanol (16 L)
6. 6
   その他dried in vacuo

実験手順

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%)

出典