Sodium Carbonate → 7-Amino-3-(5-carboxymethyl-1,3,4-oxadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid

HRID 258684Notes

Reaction equation

HRID 258684 reaction equation
[C:1]([CH2:4][C:5]1[O:6][C:7]([SH:10])=[N:8][N:9]=1)([OH:3])=[O:2].CC(O[CH2:15][C:16]1[CH2:25][S:24][C@@H:19]2[C@H:20]([NH2:23])[C:21](=[O:22])[N:18]2[C:17]=1[C:26]([OH:28])=[O:27])=O.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O.O>[NH2:23][CH:20]1[C:21](=[O:22])[N:18]2[C:17]([C:26]([OH:28])=[O:27])=[C:16]([CH2:15][S:10][C:7]3[O:6][C:5]([CH2:4][C:1]([OH:3])=[O:2])=[N:9][N:8]=3)[CH2:25][S:24][C@H:19]12

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178525247HCID 178525247, compound

Product 1

HCID 706204657-Amino-3-(5-carboxymethyl-1,3,4-oxadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

A solution of 9.61 g (0.06 mol) of 2-carboxymethyl-1,3,4-oxadiazole-5-thiol in 120 ml of acetone is added to a warm (45°) solution of 10.9 g (0.04 mol) of 7-aminocephalosporanic acid in a mixture of 220 ml of water, 50 ml of acetone and 13.44 g (0.16 mol) of sodium bicarbonate. The temperature is raised to 65° and the pH maintained at 7.4-7.6 by addition of aqueous sodium carbonate solution. After 3 hours, the acetone is removed in vacuo and the reaction mixture is cooled to 10° and adjusted to pH 3.5 by addition of dilute hydrochloric acid. The product is collected, washed with water and then acetone to give the title compound.

Workup

  1. temperatureThe temperature is raised to 65°
  2. customthe acetone is removed in vacuo
  3. temperaturethe reaction mixture is cooled to 10°
  4. additionadjusted to pH 3.5 by addition of dilute hydrochloric acid
  5. customThe product is collected
  6. washwashed with water

Sources & evidence

ORD record
ord-fb06aeffb2dc439ebf5b067d333d5175
Source dataset
uspto-grants-1977_07
Patent number
US04034092

Reaction notes

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