Hydrochloric Acid → 7beta-(2-Phenoxyacetamido)-2-oxo-3-cephem-4-carboxylic acid

HRID 66568Notes

Reaction equation

HRID 66568 reaction equation
[O:1]([CH2:8][C:9]([NH:11][C@@H:12]1[C:30](=[O:31])[N:14]2[C:15]([C:20]([O:22]CC3C=CC=CC=3)=[O:21])=[CH:16][C:17](=[O:19])[S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OC)C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl.[N+](C)([O-])=O>[O:1]([CH2:8][C:9]([NH:11][C@@H:12]1[C:30](=[O:31])[N:14]2[C:15]([C:20]([OH:22])=[O:21])=[CH:16][C:17](=[O:19])[S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 13117288Benzyl 7beta-(2-phenoxyacetamido)-2-oxo-3-cephem-4-carboxylate

Product 1

HCID 131172907beta-(2-Phenoxyacetamido)-2-oxo-3-cephem-4-carboxylic acidYield 80.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6375NitromethaneSolvent

Procedure

To a solution of benzyl 7β-(2-phenoxyacetamido)-2-oxo-3-cephem-4-carboxylate (369 mg) in methylene chloride (15 ml) were added successively anisole (1.37 ml) and a solution of aluminum chloride (560 mg) in nitromethane (5 ml) under ice-cooling. The mixture was stirred for 25 minutes at the same temperature and poured into a mixture of methylene chloride and dil. hydrochloric acid. The organic layer was separated, washed with an aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated to dryness. After addition of diisopropyl ether to the residue, the precipitates were collected by filtration and then washed with a small amount of diethyl ether to give 7β-(2-phenoxyacetamido)-2-oxo-3-cephem-4-carboxylic acid (235 mg). mp 158° to 160° C. (dec.).

Workup

  1. customThe organic layer was separated
  2. washwashed with an aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness
  5. additionAfter addition of diisopropyl ether to the residue
  6. filtrationthe precipitates were collected by filtration
  7. washwashed with a small amount of diethyl ether

Sources & evidence

ORD record
ord-fe28ccf6ed8c42dd9e63cf3531b9ffa5
Source dataset
uspto-grants-1982_08
Patent number
US04342760

Reaction notes

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