Phosphoric Acid → HCID 88839754, compound

HRID 1287816Notes

Reaction equation

HRID 1287816 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:22])(O)[O-].[Na+].P([O-])([O-])([O-])=O.[CH3:29][C:30]1[N:31]=[CH:32][S:33][CH:34]=1.[S:35]1C=CC=C1C(O)=O.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:35][C:19]([C:32]3[S:33][CH:34]=[C:30]([CH3:29])[N:31]=3)=[O:22])[CH2:15][S:14][C@H:9]12

Participants

6

Reactant 5

HCID 1004Phosphoric AcidHCID 1061PhosphateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 131710490HCID 131710490, compound

Product 1

HCID 88839754HCID 88839754, compoundYield 50.5%

Procedure

To a stirred solution of 5.4 g. (0.02 mole) of 7-aminocephalosporanic acid and 3.36 g. (0.04 mole) of sodium bicarbonate in 120 ml. of aqueous phosphate buffer (pH 6.4) was added 3.1 g. (0.02 mole) of 4-methylthiazole-2-thiolcarboxylic acid. The mixture was stirred in a nitrogen atmosphere and heated to 50°. The pH was adjusted from 7.0 to 6.5 with 42% phosphoric acid. A crystalline solid started to precipitate. After 5 hours at 50° the reaction mixture was cooled to 20°. The precipitated solid was collected by filtration, washed with water and acetone and dried in vacuo over phosphorous pentoxide 3.75 g. of crystalline yellow solid. Yield = 50.5% NMR spectrum was consistent with the structure of the title product.

Workup

  1. temperatureheated to 50°
  2. customto precipitate
  3. temperatureAfter 5 hours at 50° the reaction mixture was cooled to 20°
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water and acetone
  6. dry with materialdried in vacuo over phosphorous pentoxide 3.75 g

Sources & evidence

ORD record
ord-3a873ef9aa7548e9ab11c4bbe145e918
Source dataset
uspto-grants-1976_10
Patent number
US03985740

Reaction notes

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