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

HRID 241673

반응식

HRID 241673 반응식
[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]

참가 물질

10

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 150191Sodium Tungstate Dihydrate촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-11c93fff80824fdea864bcd3180bb5a7
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653063B2

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