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

HRID 893165Notes

Reaction equation

HRID 893165 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 11625376HCID 11625376, compound

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-fb6ec9f5cc8f40fabf25508cb9315060
Source dataset
uspto-grants-1992_06
Patent number
US05122604

Reaction notes

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