Dimethyl Sulfide → Benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate

HRID 704264Notes

Reaction equation

HRID 704264 reaction equation
[CH:1]([NH:3][CH:4]1[C:28](=[O:29])[N:6]2[CH:7]([C:12]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[C:8](=C)[CH2:9][S:10][C@H:5]12)=[O:2].[O:30]=[O+][O-].CSC>C(Cl)Cl.CO>[CH:1]([NH:3][CH:4]1[C:28](=[O:29])[N:6]2[C:7]([C:12]([O:14][CH:15]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[C:8]([OH:30])[CH2:9][S:10][C@H:5]12)=[O:2]

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 86744523Benzhydryl 7-formamido-3-methylenecepham-4-carboxylate

Product 1

HCID 88528581Benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of benzhydryl 7-formamido-3-methylenecepham-4-carboxylate (40.8 g) in methylene chloride (300 ml) and methanol (1.2 l) was cooled at -74° C. in a dry ice-acetone bath. A theoretical amount of ozone was blown through the solution at -74° C. for 10 minutes with stirring, and nitrogen gas was blown through the solution at -74° C. for 10 minutes Dimethyl sulfide (20 ml) was added to the solution at -74° C. The mixture was slowly warmed to ambient temperature and evaporated in vacuo. The residue was subjected to column chromatography on silica gel and eluted with ethyl acetate. The eluent was evaporated in vacuo to give benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate (34.4 g).

Workup

  1. customevaporated in vacuo
  2. washeluted with ethyl acetate
  3. customThe eluent was evaporated in vacuo

Sources & evidence

ORD record
ord-0d2a2342ac7d4f258d81df17c3e3f13e
Source dataset
uspto-grants-1991_01
Patent number
US04985555

Reaction notes

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