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

HRID 1730704Notes

Reaction equation

HRID 1730704 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-9a38339b6ee148b0a809fbd75f53d182
Source dataset
uspto-grants-1976_11
Patent number
US03993646

Reaction notes

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