反応 #56683

反応方程式

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

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

→

title compound

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

溶媒

brine

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise under ice-
2. 2
   温度cooling over 30 min
3. 3
   抽出The mixture was extracted with ethyl acetate (5 L)
4. 4
   洗浄The organic layer was washed with saturated brine (5 L)
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   濃縮The solvent was concentrated under reduced pressure

実験手順

4-(4-Pyridyl)-1,3-thiazole-2-thiol sodium salt (194 g, 1 mol) prepared according to the method of Reference Example 5 was suspended in tetrahydrofuran (1.5 L) and benzhydryl 7β-[(phenylacetyl)amino]-3-[(methylsulfonyl)oxy]-3-cephem-4-carboxylate (196 g, 0.91 mol) dissolved in tetrahydrofuran (3.0 L) was added dropwise under ice-cooling over 30 min. The mixture was stirred at 0° C. for 2 hr and saturated brine (7 L) was added. The mixture was extracted with ethyl acetate (5 L). The organic layer was washed with saturated brine (5 L) and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to give the title compound as crystals. The crystals were suspended in ethyl acetate (0.5 L), collected by filtration on a glass filter and washed with methanol (1 L×2). The crystals were dried in vacuo to give the title compound (412 g, 0.71 mol). yield: 78%. melting point: 134° C. Anal Calcd for C36H28N4O4S3.0.5H2O: C 63.05, H 4.11, N 8.17, S 14.02. Found: C 63.16, H 4.15, N 8.27, S 13.98. 1H-NMR(CDCl3)δ:3.41-3.73 (4H,m), 5.02 (1H,d,J=4.8 Hz), 5.84 (1H,dd,J=4.8 Hz,8.8 Hz), 6.23 (1H,d,J=8.8 Hz), 6.97 (1H,s), 7.27-7.72 (17H,m), 7.73 (1H,s), 8.67 (1H,d,J=6.2 Hz).

出典