Dimethyl Sulfoxide → HCID 66816874, compound

HRID 1755119Notes

Reaction equation

HRID 1755119 reaction equation
[C:1]([O:5][C:6](=[O:48])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][S:15]([N:18]2[CH2:23][CH2:22][C:21]([NH:26][C:27](=[O:46])[C:28]3[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[C:30]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH:29]=3)([C:24]#[N:25])[CH2:20][CH2:19]2)(=[O:17])=[O:16])=[C:9]([CH3:47])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].CS(C)=[O:51].[OH-].[Na+].OO.S([O-])([O-])(=O)=S.[Na+].[Na+].[Cl-].[NH4+]>CO>[C:1]([O:5][C:6](=[O:48])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][S:15]([N:18]2[CH2:19][CH2:20][C:21]([NH:26][C:27](=[O:46])[C:28]3[CH:33]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:31]=[C:30]([O:38][CH2:39][C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH:29]=3)([C:24](=[O:51])[NH2:25])[CH2:22][CH2:23]2)(=[O:16])=[O:17])=[C:9]([CH3:47])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 6

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 25517Ammonium ChlorideHCID 66818428HCID 66818428, compound

Product 1

HCID 66816874HCID 66816874, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-{2-[4-(3-Benzyloxy-5-trifluoromethyl-benzoylamino)-4-cyano-piperidine-1-sulfonyl]-ethyl}-3-methyl-benzoic acid tert-butyl ester (1.40 g, 2.04 mmol) was dissolved in DMSO (0.188 ml, 2.65 mmol) and methanol (7.00 ml). A 1 M aqueous sodium hydroxide solution (0.204 ml, 0.204 mmol) and aqueous hydrogen peroxide (30%, 0.265 ml, 2.65 mmol) were added under ice-cooling. The mixture was warmed to room temperature and stirred as such for two hours. After completion of the reaction, an aqueous sodium thiosulfate solution and an aqueous ammonium chloride solution were added, followed by extraction with ethyl acetate. The organic layer was washed with saline, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give 4-{2-[4-(3-benzyloxy-5-trifluoromethyl-benzoylamino)-4-carbamoyl-piperidine-1-sulfonyl]-ethyl}-3-methyl-benzoic acid tert-butyl ester as a pale yellow amorphous (1.48 g).

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c246132c23084bfa805250ff2cb5bf76
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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