Sodium Bicarbonate → rac-2-(3,5-Bis-trifluoromethyl-phenyl)-N-[(3S,4R)-1-(1,1-dioxo-1-thiomorpholine-4-carbonyl)-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-N-methyl-isobutyramide

HRID 1365924Notes

Reaction equation

HRID 1365924 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([C:13]([CH3:39])([CH3:38])[C:14]([N:16]([C@H:18]2[C@H:22]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:21][N:20]([C:30]([N:32]3[CH2:37][CH2:36]S[CH2:34][CH2:33]3)=[O:31])[CH2:19]2)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH:42][S:43]([O-:46])(=O)=O.OS(O[O-])(=O)=O.OS(O[O-])(=O)=O.[O-]S([O-])(=O)=O.[K+].[K+].[K+].[K+].[K+].OS([O-])=O.[Na+].C([O-])(O)=O.[Na+]>CO>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]([CH3:39])([CH3:38])[C:14]([N:16]([C@H:18]2[C@H:22]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH2:21][N:20]([C:30]([N:32]3[CH2:37][CH2:36][S:43](=[O:46])(=[O:42])[CH2:34][CH2:33]3)=[O:31])[CH2:19]2)[CH3:17])=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:40])[F:41])[CH:8]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 15793144Potassium caroateHCID 23665763Sodium BisulfiteHCID 59840137Rac-2-(3,5-bis-trifluoromethyl-phenyl)-n-[(3s,4r)-4-(4-fluoro-phenyl)-1-(thiomorpholine-4-carbonyl)-pyrrolidin-3-yl]-n-methyl-isobutyramide

Product 1

HCID 59840073rac-2-(3,5-Bis-trifluoromethyl-phenyl)-N-[(3S,4R)-1-(1,1-dioxo-1-thiomorpholine-4-carbonyl)-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-N-methyl-isobutyramideYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of rac-2-(3,5-bis-trifluoromethyl-phenyl)-N-[(3S,4R)-4-(4-fluoro-phenyl)-1-(thiomorpholine-4-carbonyl)-pyrrolidin-3-yl]-N-methyl-isobutyramide (0.20 g, 0.33 mmol, described herein above) in MeOH (2 ml) at RT, was added potassium monopersulfate triple salt (0.30 g, 0.49 mmol). Stirring was continued an additional 3 hours, then a solution of NaHSO3 (40%) was added, the ph was adjusted to 9 with an aqueous solution of NaHCO3, and finally the product was extracted with Et2O. Purification by flash chromatography (SiO2, EtOAc/Hx 1:1) yielded 185 mg (88%) of the title compound as_white foam.

Workup

  1. extractionfinally the product was extracted with Et2O
  2. customPurification by flash chromatography (SiO2, EtOAc/Hx 1:1)

Sources & evidence

ORD record
ord-13238c75d0764f69b0dc48b355f0f2df
Source dataset
uspto-grants-2011_02
Patent number
US07893062B2

Reaction notes

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