Hydrochloric Acid → 7-Aminodeacetoxycephalosporanic acid

HRID 27803

반응식

HRID 27803 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 334987-Aminodeacetoxycephalosporanic acid수율 89.6%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 6375Nitromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a62e99d0352f4b7ca08afd713fc9cad2
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04223132

연결된 노트

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