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Water → 1-(2-(2,3-dihydroxypropyl)-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide

HRID 1473460
ノート
印刷プレビュー

反応式

HRID 1473460 の反応式
[CH2:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[C:14]1[C:23]2[C:18](=[CH:19][C:20]([S:24]([N:27]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=3[O:42][CH3:43])[C:28]3[S:29][CH:30]=[CH:31][N:32]=3)(=[O:26])=[O:25])=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1)[CH:2]=[CH2:3].C[N+]1([O-])CC[O:48]CC1.CC(O)(C)C.[OH2:57]>[Os](=O)(=O)(=O)=O>[OH:57][CH:2]([CH2:3][OH:48])[CH2:1][C:4]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=[CH:6][C:5]=1[C:14]1[C:23]2[C:18](=[CH:19][C:20]([S:24]([N:27]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=3[O:42][CH3:43])[C:28]3[S:29][CH:30]=[CH:31][N:32]=3)(=[O:25])=[O:26])=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 866875041-(2-allyl-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide

生成物 1

HCID 866875051-(2-(2,3-dihydroxypropyl)-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide

試薬・触媒・溶媒 1

HCID 30318Osmium Tetroxide触媒

実験手順

A vial was charged with 1-(2-allyl-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide (0.114 g, 0.182 mmol), NMO (0.043 g, 0.364 mmol), t-BuOH (0.607 ml), and water (0.304 ml). Osmium tetroxide (4% aq. soln.) (0.111 ml, 0.018 mmol) was added drop wise and the reaction was stirred for two hours. The reaction was quenched with saturated sodium thiosulfate solution and diluted with ethyl acetate. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via silica gel chromatography (12 g silica gel column, gradient elution 0 to 10% MeOH:DCM) to afford 1-(2-(2,3-dihydroxypropyl)-4-(trifluoromethyl)phenyl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide as a clear oil. m/z (ESI) 660.3 (M+H)+.

後処理

  1. customThe reaction was quenched with saturated sodium thiosulfate solution
  2. additiondiluted with ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified via silica gel chromatography (12 g silica gel column, gradient elution 0 to 10% MeOH:DCM)

出典と根拠

ORDレコード
ord-727c4d123d8247e68fd4cfe054035bbc
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09012443B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート