Acetic Anhydride → (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-acetoxymethyl-4-acetylthiopyrrolidine

HRID 1088274Notes

Reaction equation

HRID 1088274 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18](=[O:20])[CH3:19])[CH2:14][C@H:13]2[CH2:21][OH:22])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1.O>[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]([S:17][C:18](=[O:20])[CH3:19])[CH2:14][C@H:13]2[CH2:21][O:22][C:25](=[O:27])[CH3:26])=[O:11])=[CH:23][CH:24]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 102695344-Nitrobenzyl (2S,4S)-4-(Acetylthio)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 15671499(2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-acetoxymethyl-4-acetylthiopyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

(2S,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-hydroxymethyl-4-acetylthiopyrrolidine (300 mg) was dissolved in 1.5 ml of dry pyridine. Acetic anhydride (1.5 ml) was added thereto. The resulting mixture was stirred at room temperature for 5 hours, diluted with water, extracted with ether, washed successively with brine, dilute hydrochloric acid, brine, a saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate and distilled to obtain (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-acetoxymethyl-4-acetylthiopyrrolidine.

Workup

  1. extractionextracted with ether
  2. washwashed successively with brine, dilute hydrochloric acid, brine
  3. dry with materiala saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate
  4. distillationdistilled

Sources & evidence

ORD record
ord-3cb9ca0c5680405080e7a5efce5f7395
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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