Hydrogen Peroxide → di-tert-butyl (2S,5S)-5-(2-benzylamino-2-carbamoylethyl)pyrrolidine-1,2-dicarboxylate

HRID 10421Notes

Reaction equation

HRID 10421 reaction equation
[CH2:1]([NH:8][CH:9]([C:30]#[N:31])[CH2:10][C@H:11]1[N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:14]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-:33].[K+].[K+].OO>CS(C)=O.O>[CH2:1]([NH:8][CH:9]([C:30](=[O:33])[NH2:31])[CH2:10][C@H:11]1[N:15]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C@H:14]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 91095133Di-tert-butyl (2s,5s)-5-(2-benzylamino-2-cyanoethyl)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 86760185di-tert-butyl (2S,5S)-5-(2-benzylamino-2-carbamoylethyl)pyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2.6 g of di-tert-butyl (2S,5S)-5-(2-benzylamino-2-cyanoethyl)pyrrolidine-1,2-dicarboxylate were dissolved in 6.5 ml of dimethyl sulfoxide. 373 mg of finely ground potassium carbonate and 1.08 ml of a 30% strength hydrogen peroxide solution were added thereto. The mixture was stirred at room temperature for 14 h and was then heated at 35° C. for 30 min. The solution was diluted with 60 ml of water and extracted 3 times with 100 ml of ethyl acetate each time. The combined organic phases were washed once with 120 ml of a saturated sodium chloride solution and dried with sodium sulfate. The solvents were removed in vacuo, and the residue was chromatographed on silica gel.

Workup

  1. temperaturewas then heated at 35° C. for 30 min
  2. extractionextracted 3 times with 100 ml of ethyl acetate each time
  3. washThe combined organic phases were washed once with 120 ml of a saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. customThe solvents were removed in vacuo
  6. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-eec8fdcdd0e0440fb1b9c9b1ae69362f
Source dataset
uspto-grants-2006_08
Patent number
US07094800B2

Reaction notes

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