2,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate → HCID 70590262, compound

HRID 1856166Notes

Reaction equation

HRID 1856166 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[SH:10].Br[CH2:12][C:13]1([CH3:39])[CH:17]([C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[O:19])[N:16]2[C:26](=[O:38])[CH:27]([NH:28][C:29](=[O:37])[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:15]2[S:14]1>P([O-])([O-])([O-])=O.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:12][C:13]1([CH3:39])[CH:17]([C:18]([O:20][CH2:21][C:22]([Cl:23])([Cl:24])[Cl:25])=[O:19])[N:16]2[C:26](=[O:38])[CH:27]([NH:28][C:29](=[O:37])[CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@H:15]2[S:14]1

Participants

5

Reactant 2

HCID 128952622,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylateHCID 178418395HCID 178418395, compound

Product 1

HCID 70590262HCID 70590262, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 312751,4-DioxaneSolvent

Procedure

Benzothiazole-2-thiol (0.20 g) was dissolved in a mixture of pH 6.7 phosphate buffer (15 ml) and dioxane (15 ml). To this solution was added 2,2,2-trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (0.54 g) and the mixture was stirred for 7 hours at room temperature. After the reaction was completed, dioxane was distilled off and the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with a 2% potassium carbonate aqueous solution and then with water and thereafter dried over magnesium sulfate. The residue obtained by distilling off the solvent was purified by column chromatography on silica gel using chloroform as developing solvent to give oily 2,2,2-trichloroethyl 2-(benzothiazol-2-yl)thiomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (0.15 g) from the second fraction of fractions each of which was separated into 30 ml.

Workup

  1. distillationdioxane was distilled off
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with a 2% potassium carbonate aqueous solution
  4. dry with materialwith water and thereafter dried over magnesium sulfate
  5. customThe residue obtained
  6. distillationby distilling off the solvent
  7. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8504dca5e6834dc8a05c442e9655b0b5
Source dataset
uspto-grants-1980_08
Patent number
US04218374

Reaction notes

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