Water → 1-(2,2-Dimethylpropionyloxy)-ethyl 3-methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate

HRID 234127Notes

Reaction equation

HRID 234127 reaction equation
[CH3:1][C:2]([CH3:10])([CH3:9])[C:3]([O:5][CH:6](I)[CH3:7])=[O:4].[CH3:11][O:12][CH2:13][C:14]1[CH2:15][S:16][C@@H:17]2[CH:24]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23](=[O:36])[N:18]2[C:19]=1[C:20]([O-:22])=[O:21].[Na+].O.C(OCC)(=O)C>CN(C)C=O>[CH3:11][O:12][CH2:13][C:14]1[CH2:15][S:16][C@@H:17]2[CH:24]([NH:25][C:26](=[O:35])[CH2:27][O:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23](=[O:36])[N:18]2[C:19]=1[C:20]([O:22][CH:6]([O:5][C:3](=[O:4])[C:2]([CH3:10])([CH3:9])[CH3:1])[CH3:7])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 133930641-Iodoethyl 2,2-dimethylpropanoateHCID 67721394Sodium 3-methoxymethyl7-phenoxyacetamido-3-cephem-4-carboxylate

Product 1

HCID 677217191-(2,2-Dimethylpropionyloxy)-ethyl 3-methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25.7 g (100 mmol) of 1-iodoethyl 2,2-dimethylpropionate are added to 42.8 g (107 mmol) of sodium 3-methoxymethyl7-phenoxyacetamido-3-cephem-4-carboxylate in 430 ml of dry dimethylformamide. The reaction mixture is stirred at room temperature for a further hour and then poured onto a mixture of 2.5 1 of water and 1.5 1 of ethyl acetate. The aqueous phase is extracted again with ethyl acetate. The combined organic phases are washed with saturated sodium chloride-solution, dried over magnesium sulfate and evaporated in vacuo.

Workup

  1. extractionThe aqueous phase is extracted again with ethyl acetate
  2. washThe combined organic phases are washed with saturated sodium chloride-solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-95706623644143b592bbac54f75c15d6
Source dataset
uspto-grants-1997_01
Patent number
US05594133

Reaction notes

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