Hydrogen Peroxide → (R)-tert-butyl 3-(1-(2-(dimethylamino)ethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)pyrrolidine-1-carboxylate

HRID 241673

Reaction equation

HRID 241673 reaction equation
[CH3:1][N:2]([CH3:32])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14][C@@H:15]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16]3)=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29].CS(O)(=O)=[O:35].OO.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+].[OH2:52]>CO.ClCCl.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:1][N:2]([CH3:32])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([C@@H:15]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:16]3)(=[O:35])=[O:52])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29]

Participants

10

Reactant 6

HCID 784Hydrogen PeroxideHCID 962WaterHCID 6395Methanesulfonic AcidHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 58513598(R)-tert-butyl 3-(1-(2-(dimethylamino)ethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylthio)pyrrolidine-1-carboxylate

Product 1

HCID 58513604(R)-tert-butyl 3-(1-(2-(dimethylamino)ethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)pyrrolidine-1-carboxylateYield 71%

Reagents, catalysts & solvents 3

HCID 150191Sodium Tungstate DihydrateCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 3-(1-(2-(dimethylamino)ethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylthio)pyrrolidine-1-carboxylate (STEP A, 802 mg, 1.74 mmol) in methanol (15 mL) was added methane-sulfonic acid (226 microL, 3.46 mmol), 30% hydrogen peroxide solution (622 microL, 6.09 mmol) and sodium tungstate dihydrate (28.7 mg, 0.0870 mmol) in water solution (0.5 mL) at 0° C. The resulting solution was stirred at room temperature for 5 h. The reaction mixture was added sodium thiosulfate aqueous solution and sodium bicarbonate aqueous solution and diluted with dichloromethane to separate. The organic layer was concentrated in vacuo. The residue was purified by amine gel column chromatography (hexane-ethyl acetate, gradient) to give the title compound (612 mg, 71%).

Workup

  1. customto separate
  2. concentrationThe organic layer was concentrated in vacuo
  3. customThe residue was purified by amine gel column chromatography (hexane-ethyl acetate, gradient)

Sources & evidence

ORD record
ord-11c93fff80824fdea864bcd3180bb5a7
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Linked notes

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