Hydrochloric Acid → 7-Aminodeacetoxycephalosporanic acid

HRID 27804

反応式

HRID 27804 の反応式
[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:10]([O:12]CC3C=CC=CC=3)=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]12.C1(OC)C=CC=CC=1.Cl>C(Cl)Cl.[N+](C)([O-])=O.[Ti](Cl)(Cl)(Cl)Cl>[NH2:1][C@@H:2]1[C:20](=[O:21])[N:4]2[C:5]([C:10]([OH:12])=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]12

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 70581629Benzyl 7beta-amino-3-methyl-3-cephem-4-carboxylate

生成物 1

HCID 334987-Aminodeacetoxycephalosporanic acid収率 32%

試薬・触媒・溶媒 3

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒HCID 6375Nitromethane溶媒

実験手順

To a solution of benzyl 7β-amino-3-methyl-3-cephem-4-carboxylate (1.2 g) and anisole (5.2 ml) in methylene chloride (100 ml) is added a solution of titanium tetrachloride (2.6 g) in nitromethane under ice cooling, and the mixture stirred for 9.5 hours at room temperature. The reaction mixture is adjusted to pH 1 or less with diluted hydrochloric acid (70 ml), washed with ethyl acetate, and neutralized with 6 N-sodium hydroxide. The resulting titanium hydroxide is removed by filtration, and the filtrate concentrated under reduced pressure at a temperature below 50° C. The resulting crystals are collected by filtration to give 7β-amino-3-methyl-3-cephem-4-carboxylic acid (270 mg). Yield: 32%. This product was identical with an authentic specimen in NMR and IR spectra.

後処理

  1. washwashed with ethyl acetate
  2. customThe resulting titanium hydroxide is removed by filtration
  3. concentrationthe filtrate concentrated under reduced pressure at a temperature below 50° C
  4. filtrationThe resulting crystals are collected by filtration

出典と根拠

ORDレコード
ord-8c3eb0c41b714b4585ddd5fc572bb3a6
出典データセット
uspto-grants-1980_09
特許番号
US04223132

関連ノート

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