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

HRID 2351133노트

반응식

HRID 2351133 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-88a90035195746d481fde2557af215ea
출처 데이터셋
uspto-grants-1989_10
특허 번호
US04871730

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