Hydrochloric Acid → HCID 13121760, compound

HRID 1678900Notes

Reaction equation

HRID 1678900 reaction equation
C(=O)(O)[O-].[Na+].[OH:6][CH2:7][C:8]1[S:12][C:11]([SH:13])=[N:10][N:9]=1.CC(O[CH2:18][C:19]1[CH2:28][S:27][C@@H:22]2[C@H:23]([NH2:26])[C:24](=[O:25])[N:21]2[C:20]=1[C:29]([OH:31])=[O:30])=O.Cl>O>[NH2:26][CH:23]1[C:24](=[O:25])[N:21]2[C:20]([C:29]([OH:31])=[O:30])=[C:19]([CH2:18][S:13][C:11]3[S:12][C:8]([CH2:7][OH:6])=[N:9][N:10]=3)[CH2:28][S:27][C@H:22]12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178520017HCID 178520017, compound

Product 1

HCID 13121760HCID 13121760, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium bicarbonate (0.84 g.) and 5-hydroxymethyl-1,3,4-thiadiazole-2-thiol (0.74 g.) were dissolved in water (40 ml.), and the solution was warmed on a water bath. To the solution was added all at once 7-aminocephalosporanic acid (1.36 g.) at 45° C. The mixture was stirred at 70°-73° C for an hour. After the reaction, the reaction mixture was cooled to 0°-5° C and adjusted to pH 5.0 with 10% hydrochloric acid. The precipitating crystals were collected by filtration to give 7-amino-3-(5-hydroxymethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (1.20 g.). m.p. 194°-199° C (dec.)

Workup

  1. temperaturethe solution was warmed on a water bath
  2. customAfter the reaction
  3. temperaturethe reaction mixture was cooled to 0°-5° C
  4. filtrationThe precipitating crystals were collected by filtration

Sources & evidence

ORD record
ord-ea46fcf7d6304f6bb1d986e90fe04f80
Source dataset
uspto-grants-1978_03
Patent number
US04077965

Reaction notes

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