Acetic Acid → 2-Methyl-7-(2-phenylthioacetamido)-3-cephem-4-carboxylic acid

HRID 1660615Notes

Reaction equation

HRID 1660615 reaction equation
C(O)(=O)C.[CH3:5][CH:6]1[CH:11]=[C:10]([C:12]([O:14]CC(Cl)(Cl)Cl)=[O:13])[N:9]2[C:20](=[O:32])[CH:21]([NH:22][C:23](=[S:31])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:8]2[S:7]1>CN(C)C=O.[Zn]>[CH3:5][CH:6]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[N:9]2[C:20](=[O:32])[CH:21]([NH:22][C:23](=[S:31])[CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C@H:8]2[S:7]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 1317112522,2,2-Trichloroethyl 2-methyl-7-(2-phenylthioacetamido)-3-cephem-4-carboxylate

Product 1

HCID 1317112552-Methyl-7-(2-phenylthioacetamido)-3-cephem-4-carboxylic acidYield 98.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 6228DimethylformamideSolvent

Procedure

Acetic acid (4.5 ml) and zinc powder (3.6 g) were added under stirring and ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-(2-phenylthioacetamido)-3-cephem-4-carboxylate (2.79 g) in anhydrous dimethylformamide (15 ml), and the mixture was stirred for 2 hours at the same temperature. After the reaction, zinc powder was filtered off, and the filtrate was poured into a mixture of 5% hydrochloric acid (75 ml) and ethyl acetate (50 ml), and extracted. The extract was washed with water and dried. After the solvent was distilled off, the residue was crystalized by adding ether to give colorless crystals of 2-methyl-7-(2-phenylthioacetamido)-3-cephem-4-carboxylic acid (2.0 g), mp 168° to 171° C. (dec.).

Workup

  1. stirringthe mixture was stirred for 2 hours at the same temperature
  2. filtrationwas filtered off
  3. additionthe filtrate was poured into a mixture of 5% hydrochloric acid (75 ml) and ethyl acetate (50 ml)
  4. extractionextracted
  5. washThe extract was washed with water
  6. customdried
  7. distillationAfter the solvent was distilled off
  8. customthe residue was crystalized
  9. additionby adding ether

Sources & evidence

ORD record
ord-1a1cb888542f46398dabb042e6909aae
Source dataset
uspto-grants-1981_12
Patent number
US04308380

Reaction notes

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