Hydrochloric Acid → HCID 70581433, compound

HRID 917976Notes

Reaction equation

HRID 917976 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.[CH3:19][C:20]1[N:24]([CH3:25])[C:23]([SH:26])=[N:22][N:21]=1.Cl>O.CC(C)=O.C([O-])(O)=O.[Na+]>[CH3:19][C:20]1[N:24]([CH3:25])[C:23]([S:26][CH2:5][C:6]2[CH2:15][S:14][C@@H:9]3[CH:10]([NH2:13])[C:11](=[O:12])[N:8]3[C:7]=2[C:16]([OH:18])=[O:17])=[N:22][N:21]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4413287-Aminocephalosporanic acidHCID 178434152HCID 178434152, compound

Product 1

HCID 70581433HCID 70581433, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×HCID 516892Sodium BicarbonateSolvent2×

Procedure

To a solution of NaHCO3 (4.2 g., 0.05 mol.) in water (50 ml.) was added 7-ACA (6.8 g., 0.025 mol.), water (50 ml.) and acetone (25 ml.). The resulting solution was warmed to 45° and then a solution of 3,4-dimethyl-5-mercapto-1,2,4-triazole (5.0 g., 0.038 mol.) in acetone (50 ml.) and 5% NaHCO3 (10 ml.) was added. The reaction was refluxed until the reaction was completed as determined by the disappearance of the acetoxy carbonyl band in the infrared absorption spectrum. During this time the pH was maintained at ca. 7.6. The solution was cooled to 10° and adjusted to pH 3.5 with 3N HCl. The precipitated product was collected, washed with acetone, and dried to give a 60% yield of 3-(3,4-dimethyl-1,2,4-triazol-5-ylthiomethyl)-7-amino-3-cephem-4-carboxylic acid.

Workup

  1. temperatureThe resulting solution was warmed to 45°
  2. temperatureThe reaction was refluxed until the reaction
  3. temperatureDuring this time the pH was maintained at ca. 7.6
  4. temperatureThe solution was cooled to 10°
  5. customThe precipitated product was collected
  6. washwashed with acetone
  7. customdried

Sources & evidence

ORD record
ord-c6d829c796aa4c648f16e8ee1eb56767
Source dataset
uspto-grants-1976_07
Patent number
US03968226

Reaction notes

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