Water → tert-butyl ((2S)-1-((2-(4-propoxyphenyl)-1-benzofuran-6-yl)oxy)propan-2-yl)carbamate

HRID 2277151Notes

Reaction equation

HRID 2277151 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:14]=3[CH:15]=2)=[CH:7][CH:6]=1)[CH2:2][CH3:3].[H-].[Na+].CC1C=CC(S(O[CH2:34][C@@H:35]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH3:36])(=O)=O)=CC=1.O>CN(C=O)C>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][C:13]3[CH:19]=[C:18]([O:20][CH2:36][C@@H:35]([NH:37][C:38](=[O:39])[O:40][C:41]([CH3:42])([CH3:44])[CH3:43])[CH3:34])[CH:17]=[CH:16][C:14]=3[CH:15]=2)=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 13200311(S)-2-((tert-butoxycarbonyl)amino)propyl 4-methylbenzenesulfonateHCID 867312072-(4-Propoxyphenyl)-1-benzofuran-6-ol

Product 1

HCID 86731206tert-butyl ((2S)-1-((2-(4-propoxyphenyl)-1-benzofuran-6-yl)oxy)propan-2-yl)carbamateYield 31.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-propoxyphenyl)-1-benzofuran-6-ol (918 mg) in DMF (10 mL) was added sodium hydride (60% oil, 137 mg), and the mixture was stirred at room temperature for 10 min. To the reaction mixture was added (2S)-2-[(tert-butoxycarbonyl)amino]propyl 4-methylbenzenesulfonate (1.13 g), and the mixture was stirred at 60° C. for 1 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was 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 (hexane/ethyl acetate) to give the title compound (460 mg).

Workup

  1. stirringthe mixture was stirred at 60° C. for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2738675bca0c4bd9990c4f5869be681f
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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