Potassium ethanethioate → HCID 54244021, compound

HRID 620782Notes

Reaction equation

HRID 620782 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10](OS(C)(=O)=O)[CH2:9][C@H:8]1[CH2:17][O:18][CH2:19][CH2:20][NH:21][C:22]([NH2:24])=[O:23])=[O:6])[CH:2]=[CH2:3].[C:25]([O-:28])(=[S:27])[CH3:26].[K+]>CN(C)C=O>[C:25]([S:27][C@@H:10]1[CH2:11][N:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[C@H:8]([CH2:17][O:18][CH2:19][CH2:20][NH:21][C:22]([NH2:24])=[O:23])[CH2:9]1)(=[O:28])[CH3:26]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 54494532HCID 54494532, compound

Product 1

HCID 54244021HCID 54244021, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2S,4R)-1-allyloxycarbonyl-4-methane- sulfonyloxy-2-[(2-ureidoethyl)oxymethyl]pyrrolidine (1.00 g) and potassium thioacetate (0.48 g) in dimethylformamide (6 ml) was heated at 80°-85° C. for 30 minutes. The mixture was poured into ice-water (30 ml) and extracted with ethyl acetate (12 ml×3). The organic layer was washed with brine (18 ml×2), dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (50 g) and eluted with a mixture of methanol and dichloromethane (5:95 v/v) to give (2S,4S)-4-acetylthio-1-allyloxycarbonyl-2-[(2-ureidoethyl)oxymethyl]pyrrolidine (0.76 g).

Workup

  1. extractionextracted with ethyl acetate (12 ml×3)
  2. washThe organic layer was washed with brine (18 ml×2)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a syrup
  6. washeluted with a mixture of methanol and dichloromethane (5:95 v/v)

Sources & evidence

ORD record
ord-161b126ed21e4cc787d9afc934619c79
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

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