Phosphoric Acid → HCID 88841109, compound

HRID 1287812Notes

Reaction equation

HRID 1287812 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.[CH3:29][C:30]1[S:34][C:33]([C:35](=[S:37])[OH:36])=[N:32][CH:31]=1.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:37][C:35]([C:33]3[S:34][C:30]([CH3:29])=[CH:31][N:32]=3)=[O:36])[CH2:15][S:14][C@H:9]12

Participants

6

Reactant 5

HCID 1004Phosphoric AcidHCID 1061PhosphateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178430595HCID 178430595, compound

Product 1

HCID 88841109HCID 88841109, compoundYield 35%

Procedure

To a stirred solution of 9.3 g. (0.034 moles) of 7-aminocephalosporanic acid and 5.75 g. (0.068 moles) of sodium bicarbonate in 204 ml. of aqueous phosphate buffer at pH 6.4 was added 5.44 g. (0.034 moles) of 5-methylthiazole-2-thiocarboxylic acid. The mixture was stirred in a nitrogen atmosphere at 50° for 5 hours keeping the pH at 6.5 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 4.4 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 4.4 g

Sources & evidence

ORD record
ord-a6439858f04c43dab20e581bda09ed8a
Source dataset
uspto-grants-1976_10
Patent number
US03985740

Reaction notes

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