Hydrochloric Acid → HCID 178511756, compound

HRID 261713Notes

Reaction equation

HRID 261713 reaction equation
[Na].[SH:2][C:3]1[NH:7][N:6]=[N:5][CH:4]=1.[OH-].[Na+].[NH2:10][C@@H:11]1[C:39](=[O:40])[N:13]2[C:14]([C:36]([OH:38])=[O:37])=[C:15]([CH2:18]OC(=O)C3C=CC=CC=3C(=O)NC(OCC)=O)[CH2:16][S:17][C@H:12]12.Cl>O.CO>[NH2:10][C@@H:11]1[C:39](=[O:40])[N:13]2[C:14]([C:36]([OH:38])=[O:37])=[C:15]([CH2:18][S:2][C:3]3[NH:7][N:6]=[N:5][CH:4]=3)[CH2:16][S:17][C@H:12]12

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 5360545SodiumHCID 705826067beta-amino-3-[2-(N-carboethoxycarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acidHCID 178527741HCID 178527741, compound

Product 1

HCID 178511756HCID 178511756, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

in water (2 ml) containing sodium salt of 5-mercapto-1H-1,2,3-triazole (120 mg) and sodium hydroxide (40 mg) is dissolved under ice cooling 7β-amino-3-[2-(N-carboethoxycarbamoyl)benzoyloxy]methyl-3-cephem-4-carboxylic acid (450 mg) and to the mixture is added diluted hydrochloric acid to adjust its pH to 5.5 under stirring, followed by further stirring for one hour at 60° C. To the solution, is added methanol (5 ml) and the mixture is allowed to cool to the room temperature. The cooled mixture is adjusted its pH to 3.9 by adding diluted hydrochloric acid under stirring and the resultant mixture is further stirred for one hour under ice-cooling. The precipitate is collected by filtration and washed with water and methanol in this order and then dried over phosphorus pentoxide. The procedure provides 7β-amino-3-(1H-1,2,3-triazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (193 mg).

Workup

  1. dissolutionis dissolved under ice
  2. stirringby further stirring for one hour at 60° C
  3. stirringunder stirring
  4. temperaturecooling
  5. filtrationThe precipitate is collected by filtration
  6. washwashed with water and methanol in this order
  7. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-9aa8b46edf954ed49f2cb643c5798b44
Source dataset
uspto-grants-1979_08
Patent number
US04166178

Reaction notes

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