Methyl morpholine oxide → HCID 67138236, compound

HRID 1592004Notes

Reaction equation

HRID 1592004 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][N:8]([CH2:12][C:13]2[S:14][C:15]([CH:18]([OH:24])[CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:16][CH:17]=2)[S:7]1(=[O:26])=[O:25].C[N+]1([O-])CCOCC1>C1COCC1.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:1][O:2][C:3]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][N:8]([CH2:12][C:13]2[S:14][C:15]([C:18](=[O:24])[CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:16][CH:17]=2)[S:7]1(=[O:25])=[O:26]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 671386072-(2,4-Dimethoxy-benzyl)-5-(5-(1-hydroxy-4-methyl-pentyl)-thiophen-2-ylmethyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Product 1

HCID 67138236HCID 67138236, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title C compound, 2-(2,4-dimethoxy-benzyl)-5-[5-(1-hydroxy-4-methyl-pentyl)-thiophen-2-ylmethyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (125 mg, 0.26 mmol) is dissolved in THF (10 mL) and 4-methylmorpholine N-oxide (152 mg, 1.3 mmol) is added. Tetrapropylammonium perruthenate (TPAP, 9 mg, 0.026 mmol) is added and the mixture is stirred at RT for 1 h. The mixture is filtered through Celite and diluted with EtOAc. The solution is washed with 1N aqueous HCl and the organic layer is dried over anhydrous MgSO4. The solvent is evaporated to afford 2-(2,4-dimethoxy-benzyl)-5-[5-(4-methyl-pentanoyl)-thiophen-2-ylmethyl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a clear oil.

Workup

  1. filtrationThe mixture is filtered through Celite
  2. additiondiluted with EtOAc
  3. washThe solution is washed with 1N aqueous HCl
  4. dry with materialthe organic layer is dried over anhydrous MgSO4
  5. customThe solvent is evaporated

Sources & evidence

ORD record
ord-31f9f25c7b3849b0a9b6821f0717df2b
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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