Sodium Sulfite → HCID 86649645, compound

HRID 1257542Notes

Reaction equation

HRID 1257542 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11](=[O:27])[C:12]2[CH:17]=[C:16]([CH:18]=C)[CH:15]=[C:14]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=3)[CH:13]=2)[CH3:9])=[N:6][CH:7]=1.I([O-])(=O)(=O)=[O:29].[Na+].S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11](=[O:27])[C:12]2[CH:13]=[C:14]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=3)[CH:15]=[C:16]([CH:18]=[O:29])[CH:17]=2)[CH3:9])=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 66895503N-[(1R)-1-(5-fluoro-2-pyridinyl)ethyl]-3-(5-methyl-2-pyridinyl)-5-vinylbenzamide

Product 1

HCID 86649645HCID 86649645, compoundYield 96.1%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[(1R)-1-(5-fluoro-2-pyridinyl)ethyl]-3-(5-methyl-2-pyridinyl)-5-vinylbenzamide (1.14 g, 3.15 mmol) in tetrahydrofuran (11 mL) and water (11 mL) were added sodium periodate (2.0 g, 9.45 mmol) and osmium tetroxide (2.5% in tert-butanol, 2.0 mL, 0.157 mmol). The reaction mixture was stirred at ambient temperature for 18 h. Saturated aqueous sodium sulfite and saturated aqueous sodium bicarbonate were added. The mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound (1.1 g). MS 364.1 (M+1).

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5ec7cdf96ff143afb90ff6eefecb10c8
Source dataset
uspto-grants-2013_06
Patent number
US08461185B2

Reaction notes

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