Phosphoric Acid → HCID 88839750, compound

HRID 1287811Notes

Reaction equation

HRID 1287811 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(=O)(O)[O-].[Na+].P([O-])([O-])([O-])=O.[S:29]1[CH:33]=[CH:32][N:31]=[C:30]1[C:34](=[S:36])[OH:35].P(=O)(O)(O)O>>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:36][C:34]([C:30]3[S:29][CH:33]=[CH:32][N:31]=3)=[O:35])[CH2:15][S:14][C@H:9]12

Participants

6

Reactant 5

HCID 1004Phosphoric AcidHCID 1061PhosphateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178526151HCID 178526151, compound

Product 1

HCID 88839750HCID 88839750, compoundYield 35%

Procedure

to a stirred solution of 9.8 g. (0.036 moles) of 7-aminocephalosporanic acid and 6.05 g. (0.072 moles) of sodium bicarbonate in 170 ml. of aqueous phosphate buffer at pH 6.4 was added 5.35 g. (0.036 moles) of thiazole-2-thiocarboxylic acid. The mixture was stirred in a nitrogen atmosphere at 50° for 5 hours keeping the pH at 6.6 with 42% phosphoric acid. Then the mixture was cooled to 20° and the precipitated solid was removed by filtration, washed with water, acetone and ether and dried in vacuo over phosphorus pentoxide to provide 4.6 g. (35% yield) of a tan crystalline solid. Infrared and NMR spectra were consistent with the structure.

Workup

  1. temperatureThen the mixture was cooled to 20°
  2. customthe precipitated solid was removed by filtration
  3. washwashed with water, acetone and ether
  4. dry with materialdried in vacuo over phosphorus pentoxide
  5. customto provide 4.6 g

Sources & evidence

ORD record
ord-f43637914060499e90dc831fa1319e85
Source dataset
uspto-grants-1976_10
Patent number
US03985740

Reaction notes

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