Water → HCID 70604033, compound

HRID 2164135Notes

Reaction equation

HRID 2164135 reaction equation
[CH3:1][S:2][CH:3]([C:24]1[O:25][CH:26]=[CH:27][CH:28]=1)[C:4]([NH:6][CH:7]1[C:22](=[O:23])[N:9]2[C:10]([C:19]([OH:21])=[O:20])=[C:11]([CH2:14]OC(=O)C)[CH2:12][S:13][C@H:8]12)=[O:5].[SH:29][C:30]1[S:31][C:32]([CH3:35])=[N:33][N:34]=1.C(=O)(O)[O-].[Na+].O>P([O-])([O-])([O-])=O>[CH3:1][S:2][CH:3]([C:24]1[O:25][CH:26]=[CH:27][CH:28]=1)[C:4]([NH:6][CH:7]1[C:22](=[O:23])[N:9]2[C:10]([C:19]([OH:21])=[O:20])=[C:11]([CH2:14][S:29][C:30]3[S:31][C:32]([CH3:35])=[N:33][N:34]=3)[CH2:12][S:13][C@H:8]12)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 70604733HCID 70604733, compoundHCID 178434161HCID 178434161, compound

Product 1

HCID 70604033HCID 70604033, compound

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Conditions

Temperature
60 °C

Procedure

7-[α-Methylthio(2-furyl)acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (341 mg), 128 mg of 2-mercapto-5-methyl-1,3,4-thiadiazole and 68 mg of sodium bicarbonate were dissolved in 10 ml of a 0.1M phosphate buffer (pH 6.4), and the solution was stirred at 60° C. for 7 hours, and then at room temperature for 14 hours. Then, 10 ml of water was added, and the mixture was washed with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid to a pH of 2, and extracted three times with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and then concentrated under reduced pressure. Petroleum ether was added to the residue, and it was powderized. By filtration, the final product was obtained.

Workup

  1. waitat room temperature for 14 hours
  2. washthe mixture was washed with diethyl ether
  3. extractionextracted three times with ethyl acetate
  4. washThe ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionPetroleum ether was added to the residue, and it
  8. filtrationBy filtration

Sources & evidence

ORD record
ord-54e3062addd84cc99e672c03200f22c9
Source dataset
uspto-grants-1979_01
Patent number
US04137406

Reaction notes

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