Sodium Acetate → HCID 12488425, compound

HRID 1834827Notes

Reaction equation

HRID 1834827 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:25](=[O:26])[N:14]2[CH:15]([C:21]([O:23][CH3:24])=[O:22])[C:16]([CH3:20])(I)[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+]>C(#N)C>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:25](=[O:26])[N:14]2[C:15]([C:21]([O:23][CH3:24])=[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

4

Reactant 2

HCID 517045Sodium AcetateHCID 70361146HCID 70361146, compound

Product 1

HCID 12488425HCID 12488425, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 7-(2-phenoxyacetamido)-3-methyl-3-iodocepham-4-carboxylate (0.25 g.) in dry acetonitrile (10 cc) and sodium acetate (45 mg.) was heated under reflux for 4 hours and concentrated. The residue was mixed with water and extracted with chloroform. The chloroform layer was washed with an aqueous sodium thiosulfate solution and then with water, dried and concentrated. The residue was subjected to chromatography on silica gel and eluated with chloroform to yield crystals (50 mg.) of methyl 7-(2-phenoxyacetamido)-3-methyl-3-cephem-4-carboxylate, m.p. 124° - 125° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. concentrationconcentrated
  4. additionThe residue was mixed with water
  5. extractionextracted with chloroform
  6. washThe chloroform layer was washed with an aqueous sodium thiosulfate solution
  7. dry with materialwith water, dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0cbb18abc4054aee87e05cf76ccc875e
Source dataset
uspto-grants-1978_01
Patent number
US04071527

Reaction notes

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