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

HRID 2286779Notes

Reaction equation

HRID 2286779 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]Br)[S:16][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl>N1C=CC=CC=1>[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:26])([Cl:27])[Cl:25])=[O:21])=[C:15]([CH3:17])[CH2:19][S:16][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6212ChloroformHCID 128952622,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

Product 1

HCID 155734262,2,2-Trichloroethyl 7-(2-phenylacetamido)-3-methyl-3-cephem-4-carboxylateYield 73.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2,2,2-trichloroethyl 6-(2-phenylacetamido)-2-methyl-2-bromomethylpenam-3-carboxylate (0.54 g.), chloroform (5 cc) and pyridine (0.16 g.) was heated under reflux for 2.5 hours. The reaction mixture was washed with water, dried over magnesium sulfate and then concentrated. The residue was crystallized from ether to yield crystals (0.34 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 2.5 hours
  3. washThe reaction mixture was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-16416b01203a4f20b1c2b2a5a5576b69
Source dataset
uspto-grants-1981_05
Patent number
US04267340

Reaction notes

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