Sodium Hydroxide → (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-aminocarbonyloxymethyl-4-mercaptopyrrolidine

HRID 1088267Notes

Reaction equation

HRID 1088267 reaction equation
[N+:1]([C:4]1[CH:33]=[CH:32][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][O:22][C:23]([NH:25]C(=O)C(Cl)(Cl)Cl)=[O:24])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+]>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][O:22][C:23]([NH2:25])=[O:24])=[O:11])=[CH:32][CH:33]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15671474(2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-trichloroacetylaminocarbonyloxymethyl-4-acetylthiopyrrolidine

Product 1

HCID 15671475(2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-aminocarbonyloxymethyl-4-mercaptopyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-trichloroacetylaminocarbonyloxymethyl-4-acetylthiopyrrolidine (121 mg) was dissolved in 5.8 ml of methanol. To the solution was added 0.45 ml of 1N sodium hydroxide solution under ice-cooling in a nitrogen stream, followed by stirring at the same temperature for 40 minutes. After neutralization by 1.45 ml of 1N hydrochloric acid, the mixture was distilled to remove methanol. The residue was diluted with methylene chloride, washed with water, dried over anhydrous sodium sulfate and distilled to obtain (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-aminocarbonyloxymethyl-4-mercaptopyrrolidine.

Workup

  1. temperaturecooling in a nitrogen stream
  2. distillationAfter neutralization by 1.45 ml of 1N hydrochloric acid, the mixture was distilled
  3. customto remove methanol
  4. additionThe residue was diluted with methylene chloride
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationdistilled

Sources & evidence

ORD record
ord-7e70d9ea3df34d238ed7658552f13afa
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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