Hydrochloric Acid → 7-Aminodeacetoxycephalosporanic acid

HRID 27803

反応式

HRID 27803 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-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl.[N+](C)([O-])=O.O>[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

8

反応物 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 70581629Benzyl 7beta-amino-3-methyl-3-cephem-4-carboxylate

生成物 1

HCID 334987-Aminodeacetoxycephalosporanic acid収率 89.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒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 dropwise added a solution of aluminum chloride (3.11 g) in nitromethane (40 ml) under ice cooling, and the mixture stirred for 4.5 hours at room temperature, mixed with water (40 ml), and adjusted to pH 0.3 with 1 N-hydrochloric acid. The aqueous layer is separated, washed with ethyl acetate (30 ml), adjusted to pH 2.4 with an aqueous solution of sodium hydroxide and allowed to stand overnight at 0° C. The resulting crystals are collected by filtration to give 7β-amino-3-methyl-3-cephem-4-carboxylic acid (757 mg). Yield: 89.6%. This product was identical with an authentic specimen in NMR and IR spectra.

後処理

  1. customThe aqueous layer is separated
  2. washwashed with ethyl acetate (30 ml)
  3. waitto stand overnight at 0° C
  4. filtrationThe resulting crystals are collected by filtration

出典と根拠

ORDレコード
ord-a62e99d0352f4b7ca08afd713fc9cad2
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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