Potassium ethanethioate → HCID 57262936, compound

HRID 1941598Notes

Reaction equation

HRID 1941598 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@H:14](OS(C)(=O)=O)[CH2:13][C@H:12]2[CH2:21][NH:22][S:23](=[O:26])(=[O:25])[NH2:24])=[O:10])=[CH:5][CH:4]=1.[C:29]([O-:32])(=[S:31])[CH3:30].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@@H:14]([S:31][C:29](=[O:32])[CH3:30])[CH2:13][C@H:12]2[CH2:21][NH:22][S:23](=[O:25])(=[O:26])[NH2:24])=[O:10])=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 23670855Potassium ethanethioateHCID 57311574HCID 57311574, compound

Product 1

HCID 57262936HCID 57262936, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of crude (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-methanesulfonyloxy-2-sulfamoylaminomethylpyrrolidine (2.26 g) obtained in Step 5 in dimethylformamide (12 ml), potassium thioacetate (1.7 g) is added. The mixture is stirred at 60° C. for 5 hours. The reaction mixture is diluted with ethyl acetate, successively washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography (toluene: ethyl acetate=1:2) to give (2S,4S)-1-p-methoxybenzyloxycarbonyl-4-acetylthio-2-sulfamoylaminomethylpyrrolidine (971 mg).

Workup

  1. washsuccessively washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by silica gel column chromatography (toluene: ethyl acetate=1:2)

Sources & evidence

ORD record
ord-0d6a13fbc75c49dd8abb5f5ce88a13db
Source dataset
uspto-grants-1997_12
Patent number
US05703243

Reaction notes

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