Hydrochloric Acid → (2S,4S)-2-(dimethylaminocarbonyl)-4-mercapto-1-(p-nitrobenzyloxycarbonyl)-1-pyrrolidine

HRID 2166271Notes

Reaction equation

HRID 2166271 reaction equation
[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17]C(=O)C)[CH2:14][C@H:13]2[C:21](=[O:25])[N:22]([CH3:24])[CH3:23])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].Cl>CO>[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]([SH:17])[CH2:14][C@H:13]2[C:21](=[O:25])[N:22]([CH3:24])[CH3:23])=[O:11])=[CH:26][CH:27]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11625376(2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-dimethylcarbamoyl-4-acetylthiopyrrolidine

Product 1

HCID 10871907(2S,4S)-2-(dimethylaminocarbonyl)-4-mercapto-1-(p-nitrobenzyloxycarbonyl)-1-pyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

40 mg of (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-dimethylcarbamoyl-4-acetylthiopyrrolidine was dissolved in 4 ml of methanol, and 0.1 ml of a 1N sodium hydroxide aqueous solution was added thereto, followed by stirring at room temperature for 15 minutes. 0.11 ml of a 1N hydrochloric acid aqueous solution was then added thereto, followed by concentration under reduced pressure. The concentrate was diluted with ethyl acetate, washed with water, dried over sodium sulfate and distilled off to remove the solvent to obtain (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-dimethylcarbamoyl-4-mercaptopyrrolidine.

Workup

  1. concentrationfollowed by concentration under reduced pressure
  2. additionThe concentrate was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. distillationdistilled off
  6. customto remove the solvent

Sources & evidence

ORD record
ord-5f0d2025139a4f40a4af9d21961e21c0
Source dataset
uspto-grants-1990_07
Patent number
US04943569

Reaction notes

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