Hydrochloric Acid → HCID 70616467, compound

HRID 1763954Notes

Reaction equation

HRID 1763954 reaction equation
[Na].CC(O[CH2:6][C:7]1[CH2:24][S:23][C@@H:10]2[C@H:11]([NH:14][C:15]([CH2:17][C:18]3[S:22][CH:21]=[CH:20][CH:19]=3)=[O:16])[C:12](=[O:13])[N:9]2[C:8]=1[C:25]([OH:27])=[O:26])=O.[SH:28][C:29]1[N:30]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:31]([CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[N:32][N:33]=1.C(=O)(O)[O-].[Na+].Cl>O>[S:22]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:17][C:15]([NH:14][CH:11]1[C:12](=[O:13])[N:9]2[C:8]([C:25]([OH:27])=[O:26])=[C:7]([CH2:6][S:28][C:29]3[N:30]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:31]([CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[N:32][N:33]=3)[CH2:24][S:23][C@H:10]12)=[O:16]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6024CephalothinHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 178525372HCID 178525372, compound

Product 1

HCID 70616467HCID 70616467, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

358 mg of the sodium salt of 7-(2-thienylacetamido)-cephalosporanic acid and 256 mg of 3-(2-mercapto-1-phenyl-1,3,4-triazol-5-yl)propionic acid were dissolved in 5 ml of water and 4.12 ml of a 0.5N aqueous solution of sodium bicarbonate. The resulting solution was heated on a water bath at 63° to 65° C. in a nitrogen atmosphere for 4.5 hours. After completion of the reaction, 5 ml of ice-water and 3 ml of 1N HCl were added to the reaction mixture while ice-cooling and stirring to precipitate white crystals, which were then filtered and washed with water. Immediately thereafter, the white crystals were throughly washed with diethyl ether to obtain 440 mg of 7-(2-thienylacetamido)-3-[5-(2-carboxyethyl)-1-phenyl-1,3,4-triazol-2-yl]thiomethyl-3-cephem-4-carboxylic acid (yield, 87.5%).

Workup

  1. temperatureThe resulting solution was heated on a water bath at 63° to 65° C. in a nitrogen atmosphere for 4.5 hours
  2. additionwere added to the reaction mixture while ice-
  3. temperaturecooling
  4. customto precipitate white crystals, which
  5. filtrationwere then filtered
  6. washwashed with water
  7. washImmediately thereafter, the white crystals were throughly washed with diethyl ether

Sources & evidence

ORD record
ord-6ad8b1d6448b4243ba076575a36e6744
Source dataset
uspto-grants-1978_09
Patent number
US04113944

Reaction notes

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