Sodium Carbonate → (2S,4R)-2-(3,5-Bis-trifluoromethyl-phenyl)-N-[6-(4-hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-4-(2-methanesulfonyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide

HRID 1951692Notes

Reaction equation

HRID 1951692 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([C:13]([CH3:41])([CH3:40])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:32]3[CH2:36][C@H:35]([OH:37])[CH2:34][C@H:33]3[CH2:38][OH:39])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2SC)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH:44][S:45]([O-:48])(=O)=O.OS(O[O-])(=O)=O.OS(O[O-])(=O)=O.[O-]S([O-])(=O)=O.[K+].[K+].[K+].[K+].[K+].S([O-])(O)=O.[Na+].[C:76](=O)([O-])[O-].[Na+].[Na+]>CO>[F:43][C:2]([F:1])([F:42])[C:3]1[CH:4]=[C:5]([C:13]([CH3:40])([CH3:41])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:32]3[CH2:36][C@H:35]([OH:37])[CH2:34][C@H:33]3[CH2:38][OH:39])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:45]([CH3:76])(=[O:48])=[O:44])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 15793144Potassium caroateHCID 23665763Sodium BisulfiteHCID 86597688(2S,4R)-2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-(4-hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-4-(2-methylsulfanyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide

Product 1

HCID 86597687(2S,4R)-2-(3,5-Bis-trifluoromethyl-phenyl)-N-[6-(4-hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-4-(2-methanesulfonyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramideYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 150 mg (0.239 mmol) (2S,4R)-2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-(4-hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-4-(2-methylsulfanyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide in 1.5 ml methanol were added 250 mg (0.406 mmol) potassium monopersulfate triple salt. The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was treated with 0.5 ml sodium hydrogen sulfite solution (38%) and stirred for 30 minutes. Addition of 5 ml 2 N sodium carbonate solution was followed by extraction with two 10-ml portions of dichloromethane. The combined organic layers were dried over sodium sulfate and purified by flash chromatography to give 131 mg (83%) of the title compound as a white foam. MS m/e (%): 660 (M+H+, 100)

Workup

  1. stirringstirred for 30 minutes
  2. extractionwas followed by extraction with two 10-ml portions of dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8bce1f7fcd424c0eadd821de12dcaf9b
Source dataset
uspto-grants-2013_03
Patent number
US08404708B2

Reaction notes

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