Water → HCID 59226047, compound

HRID 2370282Notes

Reaction equation

HRID 2370282 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([CH2:34][CH:35]=[CH2:36])[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][C:24]=2[Cl:25])[C:21]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:20][CH:19]=[CH:18]3)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH2:38].C[N+]1([O-])CCOCC1.[OH2:47]>CC(C)=O.C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([CH2:34][CH:35]([OH:47])[CH2:36][OH:38])[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][C:24]=2[Cl:25])[C:21]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:20][CH:19]=[CH:18]3)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 962WaterHCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 59226059HCID 59226059, compound

Product 1

HCID 59226047HCID 59226047, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 100 mg (0.19 mmol) of [1-allyl-4-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-cyclohexyl]-carbamic acid tert-butyl ester (52) in a mixture of 250 μL of water and 500 μL of acetone was treated with 36.2 mg (0.27 mmol) N-methylmorpholine oxide monohydrate and 24.0 μL (1.91 μmol) of a 2.5% solution of osmium tetroxide in tert-butanol. The mixture was stirred at room temperature until complete conversion was indicated by LCMS. The reaction was then quenched by addition of saturated aqueous sodium bisulfite, extracted with ethyl acetate, dried over magnesium sulfate and concentrated. 68 mg of crude [4-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-1-(2,3-dihydroxy-propyl)-cyclohexyl]-carbamic acid tert-butyl ester (56) could be isolated as mixture of stereoisomers. Rt=1.92 min (Method C). Detected mass: 557.3 (M+H+).

Workup

  1. customThe reaction was then quenched by addition of saturated aqueous sodium bisulfite
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bca0c9f0ca3b44aabc8f739a3393d6aa
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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