7-Aminocephalosporanic acid → HCID 131712722, compound

HRID 1065843Notes

Reaction equation

HRID 1065843 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([C:11]([NH2:13])=[O:12])[C:5]2[N:6]([N:8]=[N:9][N:10]=2)[N:7]=1.C(=O)(O)[O-].[Na+].CC(O[CH2:23][C:24]1[CH2:33][S:32][C@@H:27]2[C@H:28]([NH2:31])[C:29](=[O:30])[N:26]2[C:25]=1[C:34]([OH:36])=[O:35])=O>P([O-])([O-])([O-])=O>[NH2:31][CH:28]1[C:29](=[O:30])[N:26]2[C:25]([C:34]([OH:36])=[O:35])=[C:24]([CH2:23][S:1][C:2]3[CH:3]=[C:4]([C:11]([NH2:13])=[O:12])[C:5]4[N:6]([N:8]=[N:9][N:10]=4)[N:7]=3)[CH2:33][S:32][C@H:27]12

Participants

5

Reactant 3

HCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178513702HCID 178513702, compound

Product 1

HCID 131712722HCID 131712722, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Conditions

Temperature
60 °C

Procedure

To a hot solution (50°-55° C.) of 6-mercapto-8-aminocarbonyl-tetrazolo[1,5-b]pyridazine (2 g; 0.010 mole) and 2.8 g of sodium bicarbonate in 90 ml of buffer phosphate (pH 6.4), 7-ACA (4.6 g; 0.017 mole) was added portionwise and the mixture was heated at 60° C. for 4 hours. After cooling at 10° C. the precipitated 7-amino-3-[(8-aminocarbonyl-6-tetrazolo[1,5-b]pyridazinyl-thiomethyl]-3-cephem-4-carboxylic acid was collected by filtration. The solid was suspended in 150 ml of Me2CO:H2O (1:2), stirred for 30 minutes and filtered again. The collected precipitate was washed with Me2CO and dried under vacuum at 60° C. to give the title compound (80%), m.p. 228°-230° C. (dec.).

Workup

  1. filtrationwas collected by filtration
  2. filtrationfiltered again
  3. washThe collected precipitate was washed with Me2CO
  4. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-ea6b92943b084f06aa87e623e7b86ea0
Source dataset
uspto-grants-1982_05
Patent number
US04331666

Reaction notes

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