Dimethyldioxirane → 5-[2-Benzyloxy-4-(3-butyloxiranyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660713Notes

Reaction equation

HRID 660713 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[CH2:17][CH2:18][CH2:19][CH3:20])[CH:12]=[CH:11][C:10]=1[N:21]1[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)O[O:31]1>CC(C)=O.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:15]2[CH:16]([CH2:17][CH2:18][CH2:19][CH3:20])[O:31]2)[CH:12]=[CH:11][C:10]=1[N:21]1[S:25](=[O:27])(=[O:26])[NH:24][C:23](=[O:28])[CH2:22]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 115197DimethyldioxiraneHCID 688392905-[2-benzyloxy-4-((E)-hex-1-enyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Product 1

HCID 866325855-[2-Benzyloxy-4-(3-butyloxiranyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-[2-benzyloxy-4-((E)-hex-1-enyl)-phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (10 mg, 0.275 mmol) in acetone (10 mL) is added a solution of DMDO (0.56 mM, 4.9 mL, 0.413 mmol) in acetone. This mixture is stirred at RT for 1 h, at which point LCMS of the reaction shows clean conversion to the desired epoxide. The reaction mixture is diluted with EtOAc and concentrated 3× to fully remove the volatile DMDO. The remaining EtOAc is removed under reduced pressure to afford the title compound which is used directly in the next step.

Workup

  1. concentrationconcentrated 3×
  2. customto fully remove the volatile DMDO
  3. customThe remaining EtOAc is removed under reduced pressure

Sources & evidence

ORD record
ord-507f931cb60c4c7e8e902e1c41b50e8f
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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