Water → N-((2S)-1-((2-(3-fluoro-4-(3-oxobutoxy)phenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide

HRID 2277330Notes

Reaction equation

HRID 2277330 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:14]2[O:15][C:16]3[CH:21]=[C:20]([O:22][CH2:23][C@@H:24]([NH:26][C:27](=[O:29])[CH3:28])[CH3:25])[N:19]=[CH:18][C:17]=3[N:30]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH:11]([OH:13])[CH3:12].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:14]2[O:15][C:16]3[CH:21]=[C:20]([O:22][CH2:23][C@@H:24]([NH:26][C:27](=[O:29])[CH3:28])[CH3:25])[N:19]=[CH:18][C:17]=3[N:30]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][C:11](=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 86731420N-((2S)-1-((2-(3-fluoro-4-(3-hydroxybutoxy)phenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide

Product 1

HCID 86731421N-((2S)-1-((2-(3-fluoro-4-(3-oxobutoxy)phenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamideYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-((2S)-1-((2-(3-fluoro-4-(3-hydroxybutoxy)phenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide (300 mg) and Dess-Martin reagent (914 mg) in DMF (30 mL) was stirred at room temperature for 15 hr. To the mixture was added saturated aqueous sodium thiosulfate solution, and the mixture was stirred at room temperature for 10 min. Water was added thereto, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (165 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-2d26735c50a143d5873dcbdfa00d81fb
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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