Pyridine → 7-Phenoxyacetamido-3-methyl-3-cephem-4-carboxylic acid

HRID 1730703Notes

Reaction equation

HRID 1730703 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:24](=[O:25])[N:14]2[CH:15]([C:21]([OH:23])=[O:22])[C:16]([CH3:20])(Br)[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.ClCCl.S(Cl)(Cl)=O>ClC(Cl)C>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:24](=[O:25])[N:14]2[C:15]([C:21]([OH:23])=[O:22])=[C:16]([CH3:20])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 703610107-(2-Phenoxyacetamido)-3-methyl-3-bromocepham-4-carboxylic acid

Product 1

HCID 155734007-Phenoxyacetamido-3-methyl-3-cephem-4-carboxylic acidYield 11.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 7-(2-phenoxyacetamido)-3-methyl-3-bromocepham-4-carboxylic acid (860 mg.) in dry dichloroethane (20 cc) was cooled at -40° - -50° C. and pyridine and a 10% dichloromethane solution (4.7 g.) of thionyl chloride were respectively added thereto. The mixture was stirred at -40° - -50° C. for 1 hour and then at room temperature overnight, and poured into ice water and stirred for 30 minutes. The dichloroethane layer was extracted with an aqueous sodium bicarbonate solution and the aqueous layer was acidified with phosphoric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried, treated with carbon powder and then concentrated to yield crystals (80 mg.) of 7-(2-phenoxyacetamido)-3-methyl-3-cephem-4-carboxylic acid, m.p. 172° - 175° C.

Workup

  1. stirringstirred for 30 minutes
  2. extractionThe dichloroethane layer was extracted with an aqueous sodium bicarbonate solution
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. customdried
  6. additiontreated with carbon powder
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1c7041a232a84967926fcb9b5ef96f9e
Source dataset
uspto-grants-1976_11
Patent number
US03993646

Reaction notes

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