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

HRID 2351133ノート

反応式

HRID 2351133 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-88a90035195746d481fde2557af215ea
出典データセット
uspto-grants-1989_10
特許番号
US04871730

反応ノート

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