Dimethyl Sulfoxide → HCID 66673819, compound

HRID 422251Notes

Reaction equation

HRID 422251 reaction equation
OO.[C:3]([O:7][C:8](=[O:36])[N:9]([CH2:16][CH:17]1[C:26]2[C:21](=[C:22]([O:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][N:29]=3)[CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1)[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])([CH3:6])([CH3:5])[CH3:4].C([O-])([O-])=[O:38].[K+].[K+].CS(C)=O>O>[C:3]([O:7][C:8](=[O:36])[N:9]([CH2:16][CH:17]1[C:26]2[C:21](=[C:22]([O:27][C:28]3[CH:33]=[CH:32][C:31]([C:34](=[O:38])[NH2:35])=[CH:30][N:29]=3)[CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1)[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])([CH3:5])([CH3:6])[CH3:4]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 66672924HCID 66672924, compound

Product 1

HCID 66673819HCID 66673819, compoundYield 197.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 30% aq. H2O2 (239 uL) to a suspension of [5-(5-cyano-pyridin-2-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-(4-methyl-pentyl)-carbamic acid tert-butyl ester (111 mg, 0.239 mmol), K2CO3 (16 mg, 0.120 mmol) and DMSO (3 ml) stirring in an ice/water bath. After 1.5 hours, pour the reaction mixture into water and extract with EtOAc. Wash the extract with water and brine before drying (MgSO4) and concentrating to give [5-(5-Carbamoyl-pyridin-2-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-(4 methyl-pentyl)-carbamic acid tert-butyl ester (114 mg) as a white foam. Use this material without further purification.

Workup

  1. extractionextract with EtOAc
  2. washWash the
  3. extractionextract with water and brine
  4. dry with materialbefore drying (MgSO4)
  5. concentrationconcentrating

Sources & evidence

ORD record
ord-859685636cc44281a3719b900f4a8829
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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