Hydrogen Peroxide → HCID 67705629, compound

HRID 975690Notes

Reaction equation

HRID 975690 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@H:8]1[CH2:32][C:33]#[N:34])=[O:6])[CH:2]=[CH2:3].C(=O)([O-])[O-:36].[K+].[K+].OO.C(OCC)(=O)C>CS(C)=O.O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@H:8]1[CH2:32][C:33](=[O:36])[NH2:34])=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11123509HCID 11123509, compound

Product 1

HCID 67705629HCID 67705629, compoundYield 528.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (2R,4S)-1-allyloxycarbonyl-2-cyanomethyl-4-(triphenylmethylthio) pyrrolidine (1.17 g) in dimethyl sulfoxide (3.75 ml) were added potassium carbonate (50 mg) and 30% hydrogen peroxide (313 μl). After stirring at 60° C. for 2 hours, the mixture was poured into a mixture of ethyl acetate and water. The separated organic layer was washed with aqueous sodium chloride solution twice, dried over magnesium sulfate and evaporated. The residue was subjected to column chromatography on silica gel (eluent; n-hexane:ethyl acetate=1:1) to give (2R,4S)-1-allyloxycarbonyl-2-carbamoylmethyl-4-(triphenylmethylthio)pyrrolidine (0.93 g).

Workup

  1. washThe separated organic layer was washed with aqueous sodium chloride solution twice
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-1362e2d2c8504257beba0acc69fd7fb5
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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