Phosphoric Acid → 7-(5-Phthalimido-5-carboxyvaleramido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

HRID 614640Notes

Reaction equation

HRID 614640 reaction equation
[NH2:1][CH:2]([C:26]([OH:28])=[O:27])[CH2:3][CH2:4][CH2:5][C:6]([NH:8][CH:9]1[C:24](=[O:25])[N:11]2[C:12]([C:21]([OH:23])=[O:22])=[C:13]([CH2:16][O:17][C:18](=[O:20])[NH2:19])[CH2:14][S:15][C@H:10]12)=[O:7].C(N1[C:38](=[O:39])[C:37]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:36]2[C:35]1=[O:44])(OCC)=O.P(=O)(O)(O)O>P([O-])([O-])(O)=O.[K+].[K+].CC(C)=O.O>[C:35]1(=[O:44])[N:1]([CH:2]([C:26]([OH:28])=[O:27])[CH2:3][CH2:4][CH2:5][C:6]([NH:8][CH:9]2[C:24](=[O:25])[N:11]3[C:12]([C:21]([OH:23])=[O:22])=[C:13]([CH2:16][O:17][C:18](=[O:20])[NH2:19])[CH2:14][S:15][C@H:10]23)=[O:7])[C:38](=[O:39])[C:37]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:36]12

Participants

7

Reactant 3

HCID 1004Phosphoric AcidHCID 31187N-CarbethoxyphthalimideHCID 1297158037-(5-Amino-5-carboxyvaleramido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317114607-(5-Phthalimido-5-carboxyvaleramido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 24450Potassium Phosphate, DibasicSolvent

Procedure

To a stirred solution of 15 grams of 7-(5-amino-5-carboxyvaleramido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid in 150 milliliters of 10 percent potassium hydrogen phosphate buffer solution (adjusted to pH 9.1 by addition of 25 percent potassium phosphate solution) was added 9.9 grams of N-carbethoxy phthalimide in 75 milliliters of acetone. The reaction mixture was stirred at room temperature for one hour at pH 9.1, diluted with water to 300 milliliters, and the pH adjusted to 7.0 by addition of phosphoric acid. The acetone was then evaporated and the reaction mixture extracted with ethyl acetate:ethanol (88:12) to remove the phthalimide. The pH of the aqueous layers was adjusted to 2 by addition of phosphoric acid and the mixture extracted with ethyl acetate:ethanol (88:12). The extract was dried with anhydrous magnesium sulfate and filtered, and the filtrate evaporated to dryness, leaving as a residue the desired 7-(5-phthalimido-5-carboxyvaleramido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid as a foam. It was digested three times with 500-milliliter aliquots of ether. The ether washed product amounted to 17.05 grams.

Workup

  1. customThe acetone was then evaporated
  2. extractionthe reaction mixture extracted with ethyl acetate:ethanol (88:12)
  3. customto remove the phthalimide
  4. additionThe pH of the aqueous layers was adjusted to 2 by addition of phosphoric acid
  5. extractionthe mixture extracted with ethyl acetate:ethanol (88:12)
  6. dry with materialThe extract was dried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-6d1e38d2895841759985bd747c671f8a
Source dataset
uspto-grants-1979_03
Patent number
US04145538

Reaction notes

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