Hydrochloric Acid → HCID 178477385, compound

HRID 328064Notes

Reaction equation

HRID 328064 reaction equation
[NH2:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH:9]([S:11][C:12]3[NH:16][N:15]=[N:14][N:13]=3)[CH3:10])[CH2:7][S:8][C@H:3]12.C(=O)(O)[O-].[Na+].[Cl:27][CH:28]([Cl:32])[C:29](Cl)=[O:30].Cl>C(OCC)(=O)C.CC(C)=O.O>[Cl:27][CH:28]([Cl:32])[C:29]([NH:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH:9]([S:11][C:12]3[NH:13][N:14]=[N:15][N:16]=3)[CH3:10])[CH2:7][S:8][C@H:3]12)=[O:30]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6593Dichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 1784773817-Amino-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid

Product 1

HCID 178477385HCID 178477385, compoundYield 34.2%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-Amino-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (3.28 g) was suspended in a mixture (60 ml) of water and acetone (1:1) and sodium bicarbonate was added to the suspension little by little to give a solution. Dichloroacetyl chloride (3 g) was added dropwise to the solution at -5° C under stirring and the mixture was stirred at the same temperature for 30 minutes. Ethyl acetate (50 ml) was added to the reaction mixture and the mixture was adjusted to pH 2 with diluted hydrochloric acid under stirring and filtered. The ethyl acetate layer was separated from the filtrate, washed with saturated aqueous sodium chloride, dried over magnesium sulfate and then treated with activated charcoal powder. Ethyl acetate was distilled off from the solution under reduced pressure. Ether was added to the residue and the mixture was stirred overnight. Precipitates were collected by filtration to give pale yellow powder of 7-dichloroacetamido-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (1.5 g).

Workup

  1. additionwas added to the suspension little by little
  2. customto give a solution
  3. stirringthe mixture was stirred at the same temperature for 30 minutes
  4. stirringunder stirring
  5. filtrationfiltered
  6. customThe ethyl acetate layer was separated from the filtrate
  7. washwashed with saturated aqueous sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. additiontreated with activated charcoal powder
  10. distillationEthyl acetate was distilled off from the solution under reduced pressure
  11. additionEther was added to the residue
  12. stirringthe mixture was stirred overnight
  13. customPrecipitates
  14. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-4c4d6b511c324f689adb9665bd3d87ed
Source dataset
uspto-grants-1977_04
Patent number
US04016160

Reaction notes

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