Dichloroacetyl chloride → 7-Dichloroacetamido-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid

HRID 328065Notes

Reaction equation

HRID 328065 reaction equation
[NH2:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][S:10][C:11]3[S:12][C:13]([CH3:16])=[N:14][N:15]=3)[CH2:7][S:8][C@H:3]12.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[Cl:34][CH:35]([Cl:39])[C:36](Cl)=[O:37]>C(Cl)Cl>[Cl:34][CH:35]([Cl:39])[C:36]([NH:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH2:9][S:10][C:11]3[S:12][C:13]([CH3:16])=[N:14][N:15]=3)[CH2:7][S:8][C@H:3]12)=[O:37]

Participants

5

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 11708267BistrimethylsilylacetamidHCID 129420347-Amino-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 706318917-Dichloroacetamido-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acidYield 65.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-Amino-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (6.89 g) was suspended in methylene chloride (60 ml) and bis(trimethylsilyl)acetamide (8.12 g) was added to the suspension to give a solution. A solution of dichloroacetyl chloride (3.24 g) in methylene chloride (10 ml) was added to the solution obtained above at -20° C under stirring. The mixture was stirred at the same temperature for 20 minutes and methylene chloride was distilled off from the mixture after addition of a little water. Water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride and dried. The solvent was distilled off from the solution under reduced pressure. The residue was pulverized by treating with ether and precipitates were collected by filtration and dried to give 7-dichloroacetamido-3-(5-methyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (6.0 g).

Workup

  1. customto give a solution
  2. customobtained above at -20° C
  3. stirringThe mixture was stirred at the same temperature for 20 minutes
  4. distillationmethylene chloride was distilled off from the mixture
  5. additionafter addition of a little water
  6. additionWater was added to the residue
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe extract was washed with saturated aqueous sodium chloride
  9. customdried
  10. distillationThe solvent was distilled off from the solution under reduced pressure
  11. additionby treating with ether
  12. customprecipitates
  13. filtrationwere collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-f7b97888f64a407f9fd0a4f40ec74b8d
Source dataset
uspto-grants-1977_04
Patent number
US04016160

Reaction notes

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