Potassium ethanethioate → (2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-acetylthiopyrrolidine

HRID 1941580Notes

Reaction equation

HRID 1941580 reaction equation
[N+:1]([C:4]1[CH:35]=[CH:34][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15](OS(C)(=O)=O)[CH2:14][C@H:13]2[CH2:22][N:23]2[C:27](=[O:28])[C:26]3=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]3[C:24]2=[O:33])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:36]([O-:39])(=[S:38])[CH3:37].[K+]>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:38][C:36](=[O:39])[CH3:37])[CH2:14][C@H:13]2[CH2:22][N:23]2[C:27](=[O:28])[C:26]3=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]3[C:24]2=[O:33])=[O:11])=[CH:34][CH:35]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 57079827(2s,4r)-1-p-Nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-methanesulfonyloxypyrrolidine

Product 1

HCID 57106506(2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-acetylthiopyrrolidineYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2S,4R)-1-p-nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-methanesulfonyloxypyrrolidine (10 g: 19.88 mmole) and potassium thioacetate (4.54 g: 2 eq.) in dimethylformamide (60 ml) is stirred at 60° C. for 3 hours. The reaction mixture is poured into ice water (200 ml) and filtered. The precipitate is dissolved in ethyl acetate, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography (toluene: ethyl acetate) to give (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-acetylthiopyrrolidine (8.7 g). Yield: 90%.

Workup

  1. filtrationfiltered
  2. dissolutionThe precipitate is dissolved in ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel column chromatography (toluene: ethyl acetate)

Sources & evidence

ORD record
ord-6db599623c3a427c946e87e3f1594f80
Source dataset
uspto-grants-1997_12
Patent number
US05703243

Reaction notes

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