Pyridine → 2,2,2-Trichloroethyl 7-(2-phenylacetamido)-3-methyl-3-cephem-4-carboxylate

HRID 2106931Notes

Reaction equation

HRID 2106931 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[CH:14]([C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:26])[Cl:25])=[O:21])[C:15]([CH3:19])([CH2:17]Cl)[S:16][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1>ClC(Cl)CCl>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[C:14]([C:20]([O:22][CH2:23][C:24]([Cl:27])([Cl:25])[Cl:26])=[O:21])=[C:15]([CH3:19])[CH2:17][S:16][C@H:12]23)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 128952672,2,2-Trichloroethyl 2-chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

Product 1

HCID 155734262,2,2-Trichloroethyl 7-(2-phenylacetamido)-3-methyl-3-cephem-4-carboxylateYield 25.9%

Reagents, catalysts & solvents 1

HCID 65741,1,2-TrichloroethaneSolvent

Procedure

A mixture of 2,2,2-trichloroethyl 6-(2-phenylacetamido)-2-methyl-2-chloromethylpenam-3-carboxylate (0.50 g.) in 1,1,2-trichloroethane (7 cc) and pyridine (0.16 g.) was heated under reflux for 3.5 hours. After cooling, the reaction mixture was washed with water, dried and then concentrated under reduced pressure. The residue was subjected to chromatography on silica gel and eluated with chloroform. The eluate was concentrated and the residue was crystallized with ether to yield crystals (0.12 g.) of 2,2,2-trichloroethyl 7-(2-phenylacetamido)-3-methyl-3-cephem-4-carboxylate, m.p. 161°-162° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3.5 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. concentrationThe eluate was concentrated
  8. customthe residue was crystallized with ether

Sources & evidence

ORD record
ord-fcc9abda76fa41439086fc1960d3d1de
Source dataset
uspto-grants-1990_06
Patent number
US04931555

Reaction notes

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