Sodium Bicarbonate → HCID 178477378, compound

HRID 1702996Notes

Reaction equation

HRID 1702996 reaction equation
CC(O[CH2:5][C:6]1[CH2:14][S:13][C@@H:9]2[CH2:10][C:11](=[O:12])[N:8]2[C:7]=1[C:15]([OH:17])=[O:16])=O.C[N:19]1[C:23]([SH:24])=[N:22][N:21]=[N:20]1.[C:25](=O)(O)[O-].[Na+]>O.CC(C)=O>[CH3:25][CH:5]([S:24][C:23]1[NH:22][N:21]=[N:20][N:19]=1)[C:6]1[CH2:14][S:13][C@@H:9]2[CH2:10][C:11](=[O:12])[N:8]2[C:7]=1[C:15]([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 12302722Cephalosporanic AcidHCID 178482017HCID 178482017, compound

Product 1

HCID 178477378HCID 178477378, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 7-[D-N-[2-{2-N-methyl-N-phenylcarbamoyl)phenoxy}acetyl]-2-phenylglycinamido]cephalosporanic acid (3 g.), 1-methyl-1H-tetrazole-5-thiol (0.58 g.) and sodium bicarbonate (0.76 g.) in water (100 ml.) and acetone (50 ml.) was stirred at 65° to 70° C. for 6 hours, meanwhile the solution was kept at pH 7 to 7.2. After removing the insoluble substance by filtration, water was added to the filtrate to a total volume of 300 ml., treated with activated charcoal, adjusted to pH 2.0 with 10% hydrochloric acid under cooling and then extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate and then evaporated under reduced pressure the residue was crystallized with a small amount of ethyl acetate and collected by filtration to give 7-[D-N-[2-}2-(N-methyl-N-phenylcarbamoyl)phenoxy}acetyl]-2-phenylglycinamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem- 4-carboxylic acid (0.69 g.).

Workup

  1. customAfter removing the insoluble substance
  2. filtrationby filtration, water
  3. additionwas added to the filtrate to a total volume of 300 ml
  4. addition, treated with activated charcoal
  5. temperatureunder cooling
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water
  8. dry with materiala saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate
  9. customevaporated under reduced pressure the residue
  10. customwas crystallized with a small amount of ethyl acetate
  11. filtrationcollected by filtration

Sources & evidence

ORD record
ord-47389a35213b439b8f853a4b98efd19c
Source dataset
uspto-grants-1982_09
Patent number
US04350692

Reaction notes

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