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

HRID 267486Notes

Reaction equation

HRID 267486 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 hr. while maintaining the pH at 7.4-8.0 by addition of 5 percent sodium bicarbonate. 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 with water and air dried (16 g, 49 percent).

Workup

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

Sources & evidence

ORD record
ord-ad5631f407f745afa34222ac80f61193
Source dataset
uspto-grants-1976_03
Patent number
US03943127

Reaction notes

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