1,1'-(Diazomethylene)bis(benzene) → Benzhydryl 7alpha-chloro-3-methyl-3-cephem-4-carboxylate

HRID 258011ノート

反応式

HRID 258011 の反応式
[Cl:1][C@H:2]1[C:13](=[O:14])[N:4]2[C:5]([C:10]([OH:12])=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]12.[C:15]1([C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N+]=[N-])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[Cl:1][C@H:2]1[C:13](=[O:14])[N:4]2[C:5]([C:10]([O:12][CH:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]12

参加物

4

反応物 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 156604937alpha-Chloro-3-methyl-3-cephem-4-carboxylic acid

生成物 1

HCID 67657933Benzhydryl 7alpha-chloro-3-methyl-3-cephem-4-carboxylate収率 45.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

The 7α-chloro-3-methyl-3-cephem-4-carboxylic acid (10.0 g, 0.0428 mol) was dissolved in methylene chloride (200 ml), and diphenyldiazomethane (10.8 g, 0.0557 mol) dissolved in methylene chloride (50 ml) was added dropwise over 30 minutes. The mixture was stirred at room temperature for two hours. Solvent was removed under reduced pressure and the product was purified over silica column using hexane-ethyl acetate mixture to yield benzhydryl 7α-chloro-3-methyl-3-cephem-4-carboxylate (7.8 g, 45.6%). NMR (CDCl3) δ 2.1 (s, 3H, CH3), 3.25 (bs, 2H, H-2), 4.70 (bs, 1H), 4.75 (bs, 1H), 7.0 (s, 1H, CHPh2), 7.3-7.7 (m, 10H, aromatic).

後処理

  1. additionwas added dropwise over 30 minutes
  2. customSolvent was removed under reduced pressure
  3. customthe product was purified over silica column

出典と根拠

ORDレコード
ord-6fc399158cfd497cb22378f14da2f744
出典データセット
uspto-grants-1993_11
特許番号
US05264429

反応ノート

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