Phosphoric Acid → HCID 88839701, compound

HRID 1287820Notes

Reaction equation

HRID 1287820 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[S:31][CH:32]=[CH:33][N:34]=1.[K+].[S:36]1C=C(C([O-])=O)C=C1.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:19]([C:33]3[N:34]=[C:30]([CH3:29])[S:31][CH:32]=3)=[O:22])[CH2:15][S:14][C@H:9]12

Participants

6

Reactant 5

HCID 1004Phosphoric AcidHCID 1061PhosphateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 131710491HCID 131710491, compound

Product 1

HCID 88839701HCID 88839701, compoundYield 48%

Procedure

To a stirred suspension of 6.8 g. (0.025 mole) of 7-aminocephalosporanic acid and 2.1g. (0.025 mole) of sodium bicarbonate in 150 ml. of aqueous phosphate buffer (pH 6.4) was added 4.92 g. (0.025 mole) of 2-methylthiazole-4-thiolcarboxylic acid potassium salt. 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 tan solid started to precipitate. After 5 hours at 50° the reaction mixture was cooled to 20°. The solid was collected by filtration, washed with water, acetone and ether and dried in vacuo over phosphorous pentoxide to provide 4.5 g. of a tan solid. Yield = 48%. NMR spectrum was consistent with structure.

Workup

  1. additionTo a stirred suspension of 6.8 g
  2. temperatureheated to 50°
  3. customto precipitate
  4. temperatureAfter 5 hours at 50° the reaction mixture was cooled to 20°
  5. filtrationThe solid was collected by filtration
  6. washwashed with water, acetone and ether
  7. dry with materialdried in vacuo over phosphorous pentoxide
  8. customto provide 4.5 g

Sources & evidence

ORD record
ord-f4a0f7bfb0de46db84f53a6def4fc04a
Source dataset
uspto-grants-1976_10
Patent number
US03985740

Reaction notes

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