Dimethylcarbamoyl Chloride → (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-dimethylaminocarbonyloxymethyl-4-acetylthiopyrrolidine

HRID 1088268Notes

Reaction equation

HRID 1088268 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].[CH3:25][N:26]([CH3:30])[C:27](Cl)=[O:28]>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:27]([N:26]([CH3:30])[CH3:25])=[O:28])=[O:11])=[CH:23][CH:24]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 102695344-Nitrobenzyl (2S,4S)-4-(Acetylthio)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 15671476(2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-dimethylaminocarbonyloxymethyl-4-acetylthiopyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

(2S,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-hydroxymethyl-4-acetylthiopyrrolidine (78 mg) was dissolved in 1 ml of dry pyridine, and 135 mg of 4-N,N-dimethylaminopyridine and 119 mg of dimethylaminocarbonyl chloride were added successively thereto, followed by stirring at 90° to 100° C. for 20 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was 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-dimethylaminocarbonyloxymethyl-4-acetylthiopyrrolidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with water, dilute hydrochloric acid, water
  3. dry with materiala saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate
  4. distillationdistilled

Sources & evidence

ORD record
ord-cd20dd25b9554fa8905a94c3a8b621e8
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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