Hydrochloric Acid → HCID 14830205, compound

HRID 1088259Notes

Reaction equation

HRID 1088259 reaction equation
[N+:1]([C:4]1[CH:28]=[CH:27][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[CH2:21][C:22]([N:24]([CH3:26])[CH3:25])=[O: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[CH2:21][C:22]([N:24]([CH3:25])[CH3:26])=[O:23])=[O:11])=[CH:27][CH:28]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14830203(2R,4S)-1-(p-nitrobenzyloxycarbonyl)-2-dimethylaminocarbonylmethyl-4-acetylthiopyrrolidine

Product 1

HCID 14830205HCID 14830205, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2R,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-dimethylaminocarbonylmethyl-4-acetylthiopyrrolidine (100 mg) was dissolved in 3 ml of methanol, and 0.24 ml of 1N sodium hydroxide solution was added thereto under nitrogen stream at room temperature, followed by stirring at the same temperature for 15 minutes. 1N Hydrochloric acid (0.24 ml) was added thereto, followed by concentration under reduced pressure. The concentrate was diluted with methylene chloride, washed with water, dried over anhydrous sodium sulfate and distilled to remove the solvent to obtain (2R,4S)-1-(p-nitrobenzyloxycarbonyl)-2-dimethylaminocarbonylmethyl-4-mercaptopyrrolidine.

Workup

  1. customat room temperature
  2. concentrationfollowed by concentration under reduced pressure
  3. additionThe concentrate was diluted with methylene chloride
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled
  7. customto remove the solvent

Sources & evidence

ORD record
ord-55509ad636484a0881708323eea93140
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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