Water → Butyl (2R)-2-[3-[[2-benzoxazolyl[3-(4-methoxyphenoxy)propyl]amino]methyl]phenoxy]butanoate

HRID 1712176Notes

Reaction equation

HRID 1712176 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=1)[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[C@@H:43]([CH2:51][CH3:52])[C:44]([O:46][CH2:47][CH2:48][CH2:49][CH3:50])=[O:45])(=O)=O.O>C(#N)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:23][C:24]1[CH:25]=[C:26]([CH:27]=[CH:28][CH:29]=1)[O:30][C@H:43]([CH2:51][CH3:52])[C:44]([O:46][CH2:47][CH2:48][CH2:49][CH3:50])=[O:45])[CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 219497323-((Benzo[d]oxazol-2-yl(3-(4-methoxyphenoxy)propyl)amino)methyl)phenolHCID 25023368(S)-2-(Trifluoromethylsulfonyloxy)butanoic acid butyl ester

Product 1

HCID 11856280Butyl (2R)-2-[3-[[2-benzoxazolyl[3-(4-methoxyphenoxy)propyl]amino]methyl]phenoxy]butanoateYield 104.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of N-(benzoxazol-2-yl)-N-(3-(4-methoxyphenoxy)propyl)-3-hydrox ybenzylamine (530 mg) in acetonitrile (10 mL), potassium carbonate (272 mg) in a powder form was added at room temperature, and the resulting mixture was stirred for 10 minutes. The solution of n-butyl (S)-2-trifluoromethanesulfonyloxybutyrate (587 mg) in acetonitrile (10 mL) prepared in Preparative Example 6 was added to the reaction solution, and the mixture was stirred at room temperature for 14 hours. Water was added to the reaction solution, the mixture was extracted with toluene, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solution was filtered and concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain a colorless oil (748 mg, 100%).

Workup

  1. additionwas added to the reaction solution
  2. stirringthe mixture was stirred at room temperature for 14 hours
  3. extractionthe mixture was extracted with toluene
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe solution was filtered
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-d3fa7146520c4a9690ddd754bbb438fa
Source dataset
uspto-grants-2010_09
Patent number
US07790903B2

Reaction notes

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