Sodium periodate → HCID 58573346, compound

HRID 1048366Notes

Reaction equation

HRID 1048366 reaction equation
[CH2:1]([C@@:4]1([CH3:35])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=2)[N:6]([C@@H:24]([CH2:32][CH3:33])[CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:5]1=[O:34])[CH:2]=C.I([O-])(=O)(=O)=[O:37].[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[Cl:16][C:12]1[CH:11]=[C:10]([C@@H:8]2[C@@H:7]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=3)[N:6]([C@@H:24]([CH2:32][CH3:33])[CH2:25][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[C:5](=[O:34])[C@:4]([CH2:1][CH:2]=[O:37])([CH3:35])[CH2:9]2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 58573453HCID 58573453, compound

Product 1

HCID 58573346HCID 58573346, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 42 mg (0.08 mmol) of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(5-chloropyridin-2-yl)-3-methyl-1-((S)-1-morpholinobutan-2-yl)piperidin-2-one (Example 121, Step N) in THF (6 mL) and water (2 mL) added a catalytic amount of osmium tetroxide. After 3 min, 87 mg (0.41 mmol) of sodium periodate was added. The resulting white slurry was stirred at room temperature for 4.25 h, and then filtered through a fritted funnel. The filtrate was partially concentrated under reduced pressure, and then was diluted with a mixture of water and saturated aqueous sodium chloride and extracted with ethyl acetate (2×). The combined organic layers were washed with saturated aqueous sodium thiosulfate and then saturated aqueous sodium chloride. The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated. Purification of the residue by reversed phase prep. HPLC (Sunfire™ Prep C18 OBD 10 μm column (Waters, Milford, Mass.), gradient elution of 35% MeCN in water to 75% MeCN in water over a 35 min period, where both solvents contain 0.1% TFA provided the title compound as a white solid.

Workup

  1. filtrationfiltered through a fritted funnel
  2. concentrationThe filtrate was partially concentrated under reduced pressure
  3. additionwas diluted with a mixture of water and saturated aqueous sodium chloride
  4. extractionextracted with ethyl acetate (2×)
  5. washThe combined organic layers were washed with saturated aqueous sodium thiosulfate
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customPurification of the residue by reversed phase prep
  10. washHPLC (Sunfire™ Prep C18 OBD 10 μm column (Waters, Milford, Mass.), gradient elution of 35% MeCN in water to 75% MeCN in water over a 35 min period, where both solvents

Sources & evidence

ORD record
ord-6959f48602084621a7b2908b89df4530
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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