Hydrochloric Acid → 7-Aminodeacetoxycephalosporanic acid

HRID 27803

Reaction equation

HRID 27803 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 334987-Aminodeacetoxycephalosporanic acidYield 89.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6375NitromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a62e99d0352f4b7ca08afd713fc9cad2
Source dataset
uspto-grants-1980_09
Patent number
US04223132

Linked notes

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