Diazomethane → HCID 131712942, compound

HRID 1164431Notes

Reaction equation

HRID 1164431 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C:29](=[N:30][OH:31])[C:28](=[O:32])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:3])[CH3:2].[N+](=[CH2:35])=[N-]>CCOCC>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C:29](=[N:30][O:31][CH3:35])[C:28](=[O:32])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 131712943HCID 131712943, compound

Product 1

HCID 131712942HCID 131712942, compoundYield 20.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In ether (6 ml) is dissolved diphenylmethyl 3-acetoxymethyl-7-hydroxyimino-3-cephem-4-carboxylate (349 mg), and under ice-cooling, an ethereal solution of diazomethane (1 ml, 0.77 mmol) is added. While the temperature raised gradually to room temperature, the mixture is stirred for an hour. The reaction mixture is then concentrated under reduced pressure and the residue is purified by thin-layer chromatography (developer: ethyl acetate-hexane=1:1) to give diphenylmethyl 3-acetoxymethyl-7-methoxyimino-3-cephem-4-carboxylate (75 mg).

Workup

  1. temperatureunder ice-cooling
  2. concentrationThe reaction mixture is then concentrated under reduced pressure
  3. customthe residue is purified by thin-layer chromatography (developer: ethyl acetate-hexane=1:1)

Sources & evidence

ORD record
ord-8f1416c8dbec4a9d9553691cb520c680
Source dataset
uspto-grants-1983_01
Patent number
US04369312

Reaction notes

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