Potassium ethanethioate → HCID 86585071, compound

HRID 1264417Notes

Reaction equation

HRID 1264417 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:10][C@H:9]1[C:24]([N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:32]([O-:35])(=[S:34])[CH3:33].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([S:34][C:32](=[O:35])[CH3:33])[CH2:10][C@H:9]1[C:24]([N:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1)=[O:25])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 86585070HCID 86585070, compound

Product 1

HCID 86585071HCID 86585071, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.39 g (14.12 mmol) (2S,4R)-2-(Piperidine-1-carbonyl)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester in 50 ml DMF were treated with 2.42 g (21.18 mmol, 1.5 eq) potassium thioacetate at 100° C. for 4 h. The solution was concentrated in vacuo and the residue was dissolved in EtOAc, NaHCO3 solution, the phases were separated and the inorganic layer was extracted with EtOAc. The combined organic phases were washed with water and brine, dried over Na2SO4. Column chromatography gave 3.59 g (71%) (2S,4S)-4-Acetylsulfanyl-2-(piperidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as light pink solid.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. customNaHCO3 solution, the phases were separated
  4. extractionthe inorganic layer was extracted with EtOAc
  5. washThe combined organic phases were washed with water and brine
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-42c514dd077b4cbf89c760ccf545a4ef
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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