Potassium ethanethioate → HCID 86585044, compound

HRID 1264377Notes

Reaction equation

HRID 1264377 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:7][N:6]1[S:21]([C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1)(=[O:23])=[O:22])=[O:4].[C:34]([O-:37])(=[S:36])[CH3:35].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([S:36][C:34](=[O:37])[CH3:35])[CH2:7][N:6]1[S:21]([C:24]1[CH:33]=[CH:32][C:27]2[C:26](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=1)(=[O:23])=[O:22])=[O:4]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 86585045HCID 86585045, compound

Product 1

HCID 86585044HCID 86585044, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5.42 g (11 mmol) (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carboxylic acid methyl ester were suspended in 60 ml DMF and treated with 1.89 g (16.55 mmol, 1.5 eq) potassium thioacetate. The reaction mixture was heated to 100° C. for 45 min, cooled to RT and concentrated. The residue was redissolved in CH2Cl2/sat. NaHCO3 solution. The inorganic phase was extracted with EtOAc, the organic phases were washed with brine and dried over Na2SO4. After evaporation the residue was purified by column chromatography yielding 3.6 g (83%) (2S,4S)-4-Acetylsulfanyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester as orange oil, MS: 394 (MH+).

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated
  3. dissolutionThe residue was redissolved in CH2Cl2/
  4. extractionThe inorganic phase was extracted with EtOAc
  5. washthe organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter evaporation the residue
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-a55cd0d9015447b5a4851a66e314e3b6
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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