Ethyl Acetate → (S)-4-(tert-butoxycarbonyl)-1-(3-chlorophenyl)-5-[2-(ethylthio)ethyl]piperazin-2-one

HRID 342139Notes

Reaction equation

HRID 342139 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][CH2:15]OS(C)(=O)=O)[CH2:12][N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[C:10](=[O:28])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:29]([S-:31])[CH3:30].[Na+].CCOC(C)=O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][CH2:15][S:31][CH2:29][CH3:30])[CH2:12][N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[C:10](=[O:28])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4459711Sodium ethanethiolateHCID 22941056(S)-4-(tert-butoxycarbonyl)-1-(3-chlorophenyl)-5-[2-(methanesulfonyloxy)ethyl]piperazin-2-one

Product 1

HCID 67590548(S)-4-(tert-butoxycarbonyl)-1-(3-chlorophenyl)-5-[2-(ethylthio)ethyl]piperazin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the mesylate from Step F (3.6 g, 8.3 mmol) in 100 mL of DMF at 0° C. was added sodium ethanethiolate (1.4 g, 16.6 mmol). After 2 hours, the reaction was poured into EtOAc, washed with sat. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product which was used in the next step without further purification.

Workup

  1. washwashed with sat. NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09894de8d9c74912b9be17bc85430f80
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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