Aluminum(III) Chloride → (6R-(6alpha,7beta))-7-(Aminophenylacetamido)-3-chloro-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

HRID 27805Notes

Reaction equation

HRID 27805 reaction equation
[C:1]1([CH:7]([NH:31]C(OCC2C=CC=CC=2)=O)[C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:19]([O:21]CC4C=CC=CC=4)=[O:20])=[C:15]([Cl:18])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.[N+](C)([O-])=O.C(OCC)(=O)C>[C:1]1([CH:7]([C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:19]([OH:21])=[O:20])=[C:15]([Cl:18])[CH2:16][S:17][C@H:12]23)=[O:9])[NH2:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 70581884Benzyl 7beta-(alpha-phenyl-alpha-carbobenzoxyaminoacetamido)-3-chloro-3-cephem-4-carboxylate

Product 1

HCID 40958(6R-(6alpha,7beta))-7-(Aminophenylacetamido)-3-chloro-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidYield 91.4%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6375NitromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 7β-(α-phenyl-α-carbobenzoxyaminoacetamido)-3-chloro-3-cephem-4-carboxylate (295 mg) in methylene chloride (6 ml) is added a solution of aluminum chloride (267 mg) in nitromethane (3 ml) under ice cooling. After stirring for 2 hours at room temperature, the mixture is diluted with ethyl acetate, washed with dilute hydrochloric acid, and extracted with an aqueous solution of 5% sodium hydrogen carbonate. The extract is acidified with hydrochloric acid and extracted with ethyl acetate. The extract is washed with water, dried, and evaporated. The residue is recrystallized from a mixture of ethyl acetate and ether to give 7β-(α-phenyl-glycinamido)-3-chloro-3-cephem-4-carboxylic acid (167 mg). Yield: 91.4%.

Workup

  1. washwashed with dilute hydrochloric acid
  2. extractionextracted with an aqueous solution of 5% sodium hydrogen carbonate
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with water
  5. customdried
  6. customevaporated
  7. customThe residue is recrystallized from a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-c6a2abd0262b46a8b5b77f566213ccef
Source dataset
uspto-grants-1980_09
Patent number
US04223132

Reaction notes

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