HCID 70528078, compound → HCID 12834086, compound

HRID 1764020Notes

Reaction equation

HRID 1764020 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:31])[CH:12]([NH:13][C:14](=[O:30])[CH:15]([C:24]3[CH2:29][CH:28]=[CH:27][CH2:26][CH:25]=3)[NH:16]C(OC(C)(C)C)=O)[C@H:4]2[S:3]1>C(O)=O>[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:31])[CH:12]([NH:13][C:14](=[O:30])[CH:15]([C:24]3[CH2:25][CH:26]=[CH:27][CH2:28][CH:29]=3)[NH2:16])[C@H:4]2[S:3]1

Participants

3

Reactant 1

HCID 70528078HCID 70528078, compound

Product 1

HCID 12834086HCID 12834086, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 2-methyl-7-[N-(tert.-butoxycarbonyl)-2-(1,4-cyclohexadienyl)glycyl]amino-3-cephem-4-carboxylic acid (317 mg) and formic acid (3.17 ml) was stirred for 4 hours at room temperature. After the reaction was completed, formic acid was removed under reduced pressure from the reaction mixture and the residue was pulverized by adding ether. The powder was collected by filtration and dissolved in 95% acetonitrile aqueous solution (27 ml), and then the solution was stirred for an hour. Precipitates were collected by filtration and dried to give white crystals of 2-methyl-7-[2-(1,4-cyclohexadienyl)glycyl]amino-3-cephem-4-carboxylic acid (200 mg), mp 168° C. (dec.).

Workup

  1. customformic acid was removed under reduced pressure from the reaction mixture
  2. additionby adding ether
  3. filtrationThe powder was collected by filtration
  4. dissolutiondissolved in 95% acetonitrile aqueous solution (27 ml)
  5. stirringthe solution was stirred for an hour
  6. customPrecipitates
  7. filtrationwere collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-1cfe1a33cb484ac48fc0e24b0c54f147
Source dataset
uspto-grants-1978_09
Patent number
US04113940

Reaction notes

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