Hydrochloric Acid → 7-Aminodeacetoxycephalosporanic acid

HRID 27804

Reaction equation

HRID 27804 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>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

Participants

7

Reactant 3

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

Product 1

HCID 334987-Aminodeacetoxycephalosporanic acidYield 32%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 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 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.

Workup

  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

Sources & evidence

ORD record
ord-8c3eb0c41b714b4585ddd5fc572bb3a6
Source dataset
uspto-grants-1980_09
Patent number
US04223132

Linked notes

Loading…