Phosphoric Acid → 3-Carbamoyloxymethyl-7-(2-oxo-2,3-dihydrothiazol-4-yl)acetamido-3-cephem-4-carboxylic acid

HRID 127100Notes

Reaction equation

HRID 127100 reaction equation
C(=O)(O)[O-:2].[Na+].[C:6]([O:9][CH2:10][C:11]1[CH2:12][S:13][C@@H:14]2[CH:21]([NH:22][C:23](=[O:31])[CH2:24][C:25](=O)[CH2:26][S:27][C:28]#[N:29])[C:20](=[O:32])[N:15]2[C:16]=1[C:17]([OH:19])=[O:18])(=[O:8])[NH2:7].C(OCC)(=O)C.P(=O)(O)(O)O>P([O-])([O-])([O-])=O>[C:6]([O:9][CH2:10][C:11]1[CH2:12][S:13][C@@H:14]2[CH:21]([NH:22][C:23](=[O:31])[CH2:24][C:25]3[NH:29][C:28](=[O:2])[S:27][CH:26]=3)[C:20](=[O:32])[N:15]2[C:16]=1[C:17]([OH:19])=[O:18])(=[O:8])[NH2:7]

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 131712111HCID 131712111, compound

Product 1

HCID 705724003-Carbamoyloxymethyl-7-(2-oxo-2,3-dihydrothiazol-4-yl)acetamido-3-cephem-4-carboxylic acidYield 30.3%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

To a solution of sodium bicarbonate (0.067 g.) in pH 6.4 phosphate buffer (5 ml.) was gradually added 3-carbamoyloxymethyl-7-(3-oxo-4-thiocyanatobutyramido)-3-cephem-4-carboxylic acid (0.33 g.) with stirring at room temperature, and then the mixture was allowed to stand for 30 hours at room temperature. After the reaction, to the reaction mixture was added ethyl acetate (50 ml.). The reaction mixture was adjusted to pH 2 with 50% phosphoric acid, and then the ethyl acetate layer was separated therefrom. The remaining aqueous layer was further extracted with ethyl acetate. The ethyl acetate layers were combined together, washed with a saturated aqueous solution of sodium chloride dried over magnesium sulfate, treated with activated carbon and then the solvent was distilled off. The residue was pulverized in diethyl ether, collected by filtration and then dried to give 3-carbamoyloxymethyl-7-(2-oxo-2,3-dihydrothiazol-4-yl)acetamido-3-cephem-4-carboxylic acid (0.1 g.). The IR Spectrum and NMR Spectrum of this object compound were identical as those of the object compound obtained in Example 15.

Workup

  1. customAfter the reaction
  2. customthe ethyl acetate layer was separated
  3. extractionThe remaining aqueous layer was further extracted with ethyl acetate
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with activated carbon
  7. distillationthe solvent was distilled off
  8. filtrationcollected by filtration
  9. customdried

Sources & evidence

ORD record
ord-058d0a3b149e443ebce2dedbc6a67b0a
Source dataset
uspto-grants-1981_03
Patent number
US04254260

Reaction notes

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