Hydrochloric Acid → 7-Amino-3-(pyrido[2,1-c]-s-triazol-3-ylthiomethyl)-3-cephem-4-carboxylic Acid

HRID 268129Notes

Reaction equation

HRID 268129 reaction equation
[SH:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.C([O-])(O)=O.[Na+].CC(O[CH2:20][C:21]1[CH2:30][S:29][C@@H:24]2[C@H:25]([NH2:28])[C:26](=[O:27])[N:23]2[C:22]=1[C:31]([OH:33])=[O:32])=O.Cl>P([O-])([O-])([O-])=O>[NH2:28][CH:25]1[C:26](=[O:27])[N:23]2[C:22]([C:31]([OH:33])=[O:32])=[C:21]([CH2:20][S:1][C:2]3[N:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]4=[N:4][N:3]=3)[CH2:30][S:29][C@H:24]12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178527925HCID 178527925, compound

Product 1

HCID 1317101027-Amino-3-(pyrido[2,1-c]-s-triazol-3-ylthiomethyl)-3-cephem-4-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

To a hot (60°) solution of 3-mercapto-s-triazolo[4,3-a]pyridine [D. S. Tarhell et al., J. Am. Chem. Soc. 70, 1381 (1948)] (1.51 g., 10 mmole) and NaHCO3 (1.68 g., 20 mmole) in 0.1 M pH 7.4 phosphate buffer (50 ml.) was added portionwise 7-ACA (2.72 g., 10 mmole) and the mixture was heated at 80°-85° for 30 min. The reaction mixture being treated with carbon, the filtrate was acidified to pH 5 with dil. HCl to give 7-amino-3-(s-triazolo[4,3-a]pyridin-3-ylthiomethyl)-3-cephem-4-carboxylic acid which was collected by filtration, washed with water (10 ml.) and dried in vacuo on P2O5. Yield 1.40 g. (39%). M.p. 215°-220° (dec.).

Workup

  1. temperaturethe mixture was heated at 80°-85° for 30 min
  2. additionThe reaction mixture being treated with carbon

Sources & evidence

ORD record
ord-43d52a4bbbaa458c9a500caafb9b444d
Source dataset
uspto-grants-1976_03
Patent number
US03946000

Reaction notes

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