Triethylamine → (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-ethoxycarbonyloxymethyl-4-acetylthiopyrrolidine

HRID 1088275Notes

Reaction equation

HRID 1088275 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(N(CC)CC)C.Cl[C:33]([O:35][CH2:36][CH3:37])=[O:34]>ClCCl>[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:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:11])=[CH:23][CH:24]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 102695344-Nitrobenzyl (2S,4S)-4-(Acetylthio)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 15671500(2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-ethoxycarbonyloxymethyl-4-acetylthiopyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-hydroxymethyl-4-acetylthiopyrrolidine (177 mg), 76 mg of triethylamine and 61 mg of 4-N,N-dimethylaminopyridine were dissolved in 2 ml of dry dichloromethane. Ethyl chloroformate (81 mg) was added thereto under ice-cooling in a nitrogen stream. The mixture was stirred under ice-cooling for 3.5 hours, washed successively with water, dilute hydrochloric acid, water, a saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and distilled to obtain (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-ethoxycarbonyloxymethyl-4-acetylthiopyrrolidine.

Workup

  1. temperatureunder ice-cooling in a nitrogen stream
  2. temperaturecooling for 3.5 hours
  3. washwashed successively with water, dilute hydrochloric acid, water
  4. dry with materiala saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate
  5. distillationdistilled

Sources & evidence

ORD record
ord-ef0f38d6325e4a7ab72225cce527deae
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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