Hydrochloric Acid → 7-Amino-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid

HRID 2397838Notes

Reaction equation

HRID 2397838 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.[C:19](=O)(O)[O-].[Na+].C[N:25]1[C:29]([SH:30])=[N:28][N:27]=[N:26]1.Cl>O.CC(C)=O>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH:5]([S:30][C:29]3[NH:28][N:27]=[N:26][N:25]=3)[CH3:19])[CH2:15][S:14][C@H:9]12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium Bicarbonate2×HCID 178482017HCID 178482017, compound

Product 1

HCID 1784773817-Amino-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Procedure

To a suspension of 27.2 g (0.1 mol) of 7-ACA in 200 ml of water and 100 ml of acetone was added a solution of 18.9 g of sodium bicarbonate in 200 ml of water. The resultant solution was warmed on a steam bath and a solution of 14.5 g (0.125 mol) of 1-methyl-5-mercapto-1,2,3,4-tetrazole in 200 ml of acetone was added. The reaction mixture was refluxed for 3.5 hours while maintaining the pH at 7.4-8.0 by addition of 5% sodium bicarbonate solution. Acidification of the cooled reaction mixture to pH 3.5 with 6N hydrochloric acid resulted in precipitation of 7-amino-3-(1-methyl-1,2,3,4-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid which was collected, washed (H2O) and air dried (16 g, 49%).

Workup

  1. temperatureThe reaction mixture was refluxed for 3.5 hours
  2. temperaturewhile maintaining the pH at 7.4-8.0

Sources & evidence

ORD record
ord-3015ead0ffdd446f9369c649cc414460
Source dataset
uspto-grants-1977_05
Patent number
US04022895

Reaction notes

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