Reaction #56683

Reaction equation

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

Solvents

brine

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise under ice-
2. 2
   Temperaturecooling over 30 min
3. 3
   ExtractionThe mixture was extracted with ethyl acetate (5 L)
4. 4
   WashThe organic layer was washed with saturated brine (5 L)
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   ConcentrationThe solvent was concentrated under reduced pressure

Procedure

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).

Source