Phosphate → HCID 20536857, compound

HRID 1156147Notes

Reaction equation

HRID 1156147 reaction equation
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[NH2:19][N:20]1[C:24]([N:25]2[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:28][C:27]([CH3:36])=[N:26]2)=[N:23][N:22]=[C:21]1[SH:37].C(=O)(O)[O-].[Na+].P([O-])([O-])([O-])=O>>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[CH:9]1[S:14][CH2:15][C:6]([CH2:5][S:37][C:21]1[N:20]([NH2:19])[C:24]([N:25]3[C:29]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:28][C:27]([CH3:36])=[N:26]3)=[N:23][N:22]=1)=[C:7]2[C:16]([OH:18])=[O:17]

Participants

5

Reactant 4

HCID 1061PhosphateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178422624HCID 178422624, compound

Product 1

HCID 20536857HCID 20536857, compound

Conditions

Temperature
60 °C

Procedure

A mixture of 1.36 g. of 7-aminocephalosporanic acid, 1.50 g. of 4-amino-5-(3-methyl-5-phenyl-1-pyrazolyl)-4H-1,2,4-triazole-3-thiol and 0.84 g. of sodium bicarbonate in 40 ml. of pH 6.4 phosphate buffer is stirred and heated at 60° C. for 8 hours. The mixture is cooled to room temperature, filtered and the filtrate is extracted with ethyl acetate. The aqueous portion is acidified to pH 2.5 with 4 N hydrochloric acid. The precipitate is collected by filtration and dried, giving 0.8 g. of the desired product, I.R. 5.60μ (β-lactam carbonyl).

Workup

  1. additionA mixture of 1.36 g
  2. temperatureThe mixture is cooled to room temperature
  3. filtrationfiltered
  4. extractionthe filtrate is extracted with ethyl acetate
  5. filtrationThe precipitate is collected by filtration
  6. customdried
  7. customgiving 0.8 g

Sources & evidence

ORD record
ord-dd5ce7000bb4486886d2112923b26885
Source dataset
uspto-grants-1982_06
Patent number
US04334062

Reaction notes

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