Potassium Carbonate → Benzhydryl 7-formamido-3-mesyloxy-3-cephem-4-carboxylate

HRID 704261ノート

反応式

HRID 704261 の反応式
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH:12]([NH:14][CH:15]1[C:39](=[O:40])[N:17]2[C:18]([C:23]([O:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])=[C:19]([OH:22])[CH2:20][S:21][C@H:16]12)=[O:13]>CN(C)C=O>[CH:12]([NH:14][CH:15]1[C:39](=[O:40])[N:17]2[C:18]([C:23]([O:25][CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:24])=[C:19]([O:22][S:1]([CH3:4])(=[O:3])=[O:2])[CH2:20][S:21][C@H:16]12)=[O:13]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chloride2 回HCID 88528581Benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate

生成物 1

HCID 88528775Benzhydryl 7-formamido-3-mesyloxy-3-cephem-4-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
-30 °C

実験手順

Mesyl chloride (0.66 ml) and potassium carbonate (1.38 g) were added to a solution of benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate (2.05 g) in N,N-dimethylformamide (6 ml) at -30° C. The mixture was stirred at -30° C. for 30 minutes. Mesyl chloride (0.4 ml) was added to the mixture. The reaction mixture was stirred at -30° C. for 20 minutes, poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and filtered, and the filtrate was evaporated in vacuo. The residue was dissolved in a small amount of ethyl acetate and the mixture was subjected to column chromatography on silica gel and eluted with a mixture of benzene and ethyl acetate (1:1). The eluent was evaporated in vacuo. The residue was triturated with diisopropyl ether to give benzhydryl 7-formamido-3-mesyloxy-3-cephem-4-carboxylate (0.85 g).

後処理

  1. stirringThe reaction mixture was stirred at -30° C. for 20 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo
  7. dissolutionThe residue was dissolved in a small amount of ethyl acetate
  8. washeluted with a mixture of benzene and ethyl acetate (1:1)
  9. customThe eluent was evaporated in vacuo
  10. customThe residue was triturated with diisopropyl ether

出典と根拠

ORDレコード
ord-0da1846da2e04d90ae4f05bb7803ae7f
出典データセット
uspto-grants-1991_01
特許番号
US04985555

反応ノート

読み込み中…