Sodium Carbonate → 3-Methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylic acid

HRID 1979785Notes

Reaction equation

HRID 1979785 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:27])[CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15](=[O:28])[N:10]2[C:11]=1[C:12]([O-:14])=[O:13])(=O)C.[Na+].[Br-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:1][O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:27])[CH2:19][O:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:15](=[O:28])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 253881Sodium BromideHCID 23673564Sodium 3-acetoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate

Product 1

HCID 159176843-Methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylic acidYield 79.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

2 g of sodium 3-acetoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate were dissolved in 20 ml of 35% v/v aqueous methanol, and 16 g of sodium bromide were added to the resulting solution. The mixture was stirred at 70° C. for 2 hours, after which it was diluted with 20 ml of ice-water, neutralised by the addition of a saturated aqueous solution of sodium carbonate and then extracted twice, each time with 50 ml of ethyl acetate. The aqueous phase was acidified by the addition of a saturated aqueous solution of potassium hydrogen sulphate and then again extracted twice, each time with 50 ml of ethyl acetate. All of the ethyl acetate extracts were combined and the combined extracts were washed with an aqueous solution of sodium chloride, dehydrated over anhydrous magnesium sulphate and then concentrated by evaporation under reduced pressure to give 1.4 g of 3-methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylic acid, in the form of a yellow solid.

Workup

  1. additionwere added to the resulting solution
  2. extractionextracted twice
  3. additionThe aqueous phase was acidified by the addition of a saturated aqueous solution of potassium hydrogen sulphate
  4. extractionagain extracted twice
  5. washthe combined extracts were washed with an aqueous solution of sodium chloride
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-a5855b5cdc0b47ea87a74e41a9af7d04
Source dataset
uspto-grants-1984_11
Patent number
US04482710

Reaction notes

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