Methyl morpholine oxide → HCID 10141054, compound

HRID 896695Notes

Reaction equation

HRID 896695 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH:4]([C:25]1[CH:30]=[CH:29][C:28](SC)=[CH:27][CH:26]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:13]=[C:14]([CH:22]([CH3:24])[CH3:23])[CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)[CH:7]=1.[CH3:34][N+]1([O-])CCOCC1.[S:42](S([O-])=O)([O-:45])(=O)=[O:43].[Na+].[Na+]>C1COCC1.C(OCC)(=O)C.O=[Os](=O)(=O)=O>[CH3:1][O:2][C:3](=[O:33])[CH:4]([C:25]1[CH:30]=[CH:29][C:28]([S:42]([CH3:34])(=[O:45])=[O:43])=[CH:27][CH:26]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:13]=[C:14]([CH:22]([CH3:24])[CH3:23])[CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)[CH:7]=1

Participants

7

Reactant 3

HCID 82029Methyl morpholine oxideHCID 656671Sodium PyrosulfiteHCID 69693881HCID 69693881, compound

Product 1

HCID 10141054HCID 10141054, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[3-(6-isopropyl-quinolin-8-yl)-phenyl]-2-(4-methylsulfanyl-phenyl)-propionic acid methyl ester from Step 1 (1.05 g, 2.3 mmol), NMO (655 mg, 4.85 mmol) and OsO4 (4%, H2O, 1 mL, 0.16 mmol) in THF (20 mL) was stirred 18 h at 21° C. The resulting reaction mixture was diluted with a sodium metabisulfite solution and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 80:20) provided the 3-[3-(6-isopropyl-quinolin-8-yl)-phenyl]-2-(4-methanesulfonyl-phenyl)-propionic acid methyl ester compound.

Workup

  1. customThe resulting reaction mixture
  2. washThe organic extracts were washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with hexane/ethyl acetate, 80:20)

Sources & evidence

ORD record
ord-6bb474ec4f524248a98843ffc522667a
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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