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

HRID 241673

Reaktionsgleichung

Reaktionsgleichung von HRID 241673
[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]

Komponenten

10

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 150191Sodium Tungstate DihydrateKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-11c93fff80824fdea864bcd3180bb5a7
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653063B2

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