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

HRID 1730706

Reaction equation

HRID 1730706 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])([CH2:18]Br)[S:17][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.C[Si](Cl)(C)C.C(OCC)(=O)C>C1C=CC=CC=1>[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])[CH2:18][S:17][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 1049Pyridine2×HCID 6397ChlorotrimethylsilaneHCID 8857Ethyl AcetateHCID 128952582-Bromomethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylic acid

Product 1

HCID 155734007-Phenoxyacetamido-3-methyl-3-cephem-4-carboxylic acidYield 71.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

6-(2-phenoxyacetamido)-2-methyl-2-bromomethylpenam-3-carboxylic acid (429 mg.) was suspended in dry benzene (10 cc), and pyridine (400 mg.) and trimethylsilylchloride (5 cc) were added thereto. The mixture was stirred for 1.5 hours at room temperature and pyridine (400 mg.) was added thereto. The mixture was heated under reflux for 3 hours, mixed with ethyl acetate (30 cc), washed with dilute phosphoric acid and further with an aqueous solution saturated with sodium chloride, dried and then concentrated. A small amount of ethyl acetate was added to the residue and the precipitate was collected by filtration to yield crystals (250 mg.) of 7-(2-phenoxyacetamido)-3-methyl-3-cephem-4-carboxylic acid, m.p. 170.5° - 172° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. washwashed with dilute phosphoric acid and further with an aqueous solution saturated with sodium chloride
  4. customdried
  5. concentrationconcentrated
  6. additionA small amount of ethyl acetate was added to the residue
  7. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-62db17ec99264e02a0c05500f94c7238
Source dataset
uspto-grants-1976_11
Patent number
US03993646

Linked notes

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