Sodium hydride → HCID 58355207, compound

HRID 1184244Notes

Reaction equation

HRID 1184244 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[C:20]([CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26])=[C:19]([C:27]([N:29]([CH2:45][CH:46]([CH3:48])[CH3:47])[C@H:30]2[CH2:35][C@@H:34]([CH:36]=[O:37])[CH2:33][N:32]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:31]2)=[O:28])[N:18]=[N:17]1>CS(C)=O.C(=O)([O-])O.[Na+]>[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[C:20]([CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26])=[C:19]([C:27]([N:29]([CH2:45][CH:46]([CH3:48])[CH3:47])[C@H:30]2[CH2:35][C@@H:34]([CH:36]3[CH2:2][O:37]3)[CH2:33][N:32]([C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])[CH2:31]2)=[O:28])[N:18]=[N:17]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 58355275HCID 58355275, compound

Product 1

HCID 58355207HCID 58355207, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Trimethylsulfoxonium iodide (390 mg) was dissolved in DMSO (5 ml), sodium hydride (50% in oil, 85 mg) was added, and the mixture was stirred at room temperature for 1 hr. A solution (10 ml) of tert-butyl(3S,5R)-3-[{[1-(2-fluorophenyl)-5-(4-methoxybutyl)-1H-1,2,3-triazol-4-yl]carbonyl}(2-methylpropyl)amino]-5-formylpiperidine-1-carboxylate (656 mg) in DMSO was added to the reaction mixture, and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (10:90-100:0) was concentrated under reduced pressure to give the object product (372 mg).

Workup

  1. stirringthe mixture was further stirred at room temperature for 1 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washa fraction eluted with ethyl acetate-hexane (10:90-100:0)
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-c74e16904f5c41ec8e1954f9e8841f56
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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