Phosphate → 7-Amino-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 268126Notes

Reaction equation

HRID 268126 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.P([O-])([O-])([O-])=O.C([O-])(O)=O.[Na+].[SH:29][C:30]1[S:31][C:32]([CH3:35])=[N:33][N:34]=1>>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:29][C:30]3[S:31][C:32]([CH3:35])=[N:33][N:34]=3)[CH2:15][S:14][C@H:9]12

Participants

5

Reactant 4

HCID 1061PhosphateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178434161HCID 178434161, compound

Product 1

HCID 129420347-Amino-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of 2.72 g. (0.01 mole) of 7-ACA in 50 ml. of 0.1 M, pH 6.4 phosphate buffer, was added 1.68 g. (0.02 mole) of NaHCO3 followed by 1.45 g. (0.011 mole) of 2-mercapto-5-methyl-1,3,4-thiadiazole and the mixture heated and stirred at 60° C. for five hours. The resulting slurry was then allowed to cool to about 22° C. over a one hour period. The crystalline precipitate was collected by filtration, washed with water and air dried. Yield 1.3 g., dec. pt. 206° C. Scaling up the reaction 10X gave 18.0 g.

Workup

  1. additionTo a stirred suspension of 2.72 g
  2. temperatureto cool to about 22° C. over a one hour period
  3. filtrationThe crystalline precipitate was collected by filtration
  4. washwashed with water and air
  5. customdried
  6. customScaling up the reaction 10X
  7. customgave 18.0 g

Sources & evidence

ORD record
ord-f00013e30b9e421bb431bfb944d22c0b
Source dataset
uspto-grants-1976_03
Patent number
US03946000

Reaction notes

Loading…