Hydrochloric Acid → HCID 178525245, compound

HRID 1763953Notes

Reaction equation

HRID 1763953 reaction equation
C(=O)(O)[O-].[Na+].[SH:6][C:7]1[NH:8][C:9]([CH2:12][C:13]([O-:15])=[O:14])=[N:10][N:11]=1.O.Cl.CC(O[CH2:22][C:23]1[CH2:40][S:39][C@@H:26]2[C@H:27]([NH:30][C:31]([CH2:33][C:34]3[S:38][CH:37]=[CH:36][CH:35]=3)=[O:32])[C:28](=[O:29])[N:25]2[C:24]=1[C:41]([OH:43])=[O:42])=O>[Na]>[S:38]1[CH:37]=[CH:36][CH:35]=[C:34]1[CH2:33][C:31]([NH:30][CH:27]1[C:28](=[O:29])[N:25]2[C:24]([C:41]([OH:43])=[O:42])=[C:23]([CH2:22][S:6][C:7]3[NH:8][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[N:10][N:11]=3)[CH2:40][S:39][C@H:26]12)=[O:32]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6024CephalothinHCID 516892Sodium BicarbonateHCID 178525246HCID 178525246, compound

Product 1

HCID 178525245HCID 178525245, compound

Reagents, catalysts & solvents 1

HCID 5360545SodiumSolvent

Procedure

12 ml of a 0.5N aqueous solution of sodium bicarbonate was dissolved in a mixture of 836 mg of the sodium salt of 7-(2-thienylacetamido)cephalosporanic acid, 480 mg of 2-(2-mercapto-1,3,4-triazol-5-yl)acetate and 5 ml of water. The resulting solution was heated to a temperature of 62° to 65° C. for 5.5 hours. After completion of the reaction, 10 ml of ice-water was added to the reaction mixture, and 8 ml of 1N HCl was slowly added thereto under ice-cooling and stirring. The precipitated white mass was filtered and washed with water. Immediately thereafter, the precipitate was pulverized with a sufficient amount of diethyl ether to obtain 810 ml of 7-(2-thienylacetamido)-3-(5-carboxymethyl-1,3,4-triazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid as a white powder.

Workup

  1. temperatureThe resulting solution was heated to a temperature of 62° to 65° C. for 5.5 hours
  2. additionwas slowly added
  3. temperatureunder ice-cooling
  4. filtrationThe precipitated white mass was filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-0fef3dd1c85f43d78f846d5aa4a20a14
Source dataset
uspto-grants-1978_09
Patent number
US04113944

Reaction notes

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