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

HRID 241673

反応式

HRID 241673 の反応式
[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]

参加物

10

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 150191Sodium Tungstate Dihydrate触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-11c93fff80824fdea864bcd3180bb5a7
出典データセット
uspto-grants-2014_02
特許番号
US08653063B2

関連ノート

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