Sodium Bicarbonate → HCID 70378459, compound

HRID 1389680Notes

Reaction equation

HRID 1389680 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([OH:28])=[O:27])=[C:15]([CH2:18]OC(=O)CC(=O)C)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[SH:31][C:32]1[N:36]([CH3:37])[N:35]=[N:34][N:33]=1.C(=O)(O)[O-].[Na+]>O>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([OH:28])=[O:27])=[C:15]([CH2:18][S:31][C:32]4[N:36]([CH3:37])[N:35]=[N:34][N:33]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 70542212HCID 70542212, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 70378459HCID 70378459, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 50 ml of water was dissolved 4.32 g of 7-phenylacetamido-3-(3-oxobutyryloxy)methyl-3-cephem-4-carboxylic acid, together with 1.50 g of 5-mercapto-1-methyl-1H-tetrazole and 1.68 g of sodium bicarbonate and the reaction was conducted at 60° C. for 50 minutes. After cooling, the reaction mixture was adjusted to pH 5.0 and washed with ethyl acetate. It was then brought down to pH 2.0 and extracted three times with ethyl acetate. The ethyl acetate solution was washed with a saturated aqueous solution of sodium chloride, treated with magnesium sulfate, filtered and distilled under reduced pressure to remove the solvent. The residue was recrystallized from ethyl acetate-ether. The procedure provided 4.29 g (yield 96.2%) of 7-phenylacetamido-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid.

Workup

  1. temperatureAfter cooling
  2. washwashed with ethyl acetate
  3. extractionextracted three times with ethyl acetate
  4. washThe ethyl acetate solution was washed with a saturated aqueous solution of sodium chloride
  5. additiontreated with magnesium sulfate
  6. filtrationfiltered
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customThe residue was recrystallized from ethyl acetate-ether

Sources & evidence

ORD record
ord-e94ad9f02c2d48df8f6b3208b526fd08
Source dataset
uspto-grants-1981_01
Patent number
US04245088

Reaction notes

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