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

HRID 1473460Notes

Reaction equation

HRID 1473460 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-727c4d123d8247e68fd4cfe054035bbc
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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