Hydrogen Peroxide → HCID 86619146, compound

HRID 2238681Notes

Reaction equation

HRID 2238681 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[CH2:17])=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH:19]12B[CH:23]([CH2:24][CH2:25][CH2:26]1)[CH2:22][CH2:21]C2.[OH-:28].[Na+].[OH:30]O>O1CCCC1.O>[C:1]([O:5][C:6]([NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][O:28][C:19](=[O:30])[C:26]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:12][CH:11]=1)[CH3:9])=[O:18])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 59861741HCID 59861741, compound

Product 1

HCID 86619146HCID 86619146, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

24.2 mg of the t-butyl[(1S)-1-(4-vinylphenyl)ethyl]carbamate [152-1] was dissolved in 1 mL of tetrahydrofuran, then 783 μL of 9-borabicyclo[3.3.1]nonane (9-BBN, 0.5M tetrahydrofuran solution) was added dropwise over 2 minutes under an ice-cold condition, and stirred overnight at room temperature. Thereto, 0.2 mL of a 3N aqueous solution of sodium hydroxide and 0.2 mL of hydrogen peroxide solution (35%) were added, and stirred at room temperature for 10 hours. The reaction mixture was added with water and extracted with chloroform, and the organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by preparative thin-layer chromatography. The obtained compound was dissolved in 1.5 mL of N,N-dimethylformamide, then 14.2 mg of benzoic acid and 21.3 mg of 4-dimethylaminopyridine were added and stirred to homogenize the solution, and 22.3 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added and stirred overnight at room temperature. Thereto, water was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the thus obtained residue was purified by preparative thin-layer chromatography, to obtain 15.2 mg of 2-(4-{(1S)-1-[(t-butoxycarbonyl)amino]ethyl}phenyl)ethylbenzoate [152-2] as a white solid.

Workup

  1. stirringstirred at room temperature for 10 hours
  2. extractionextracted with chloroform
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insolubles were filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe obtained residue was purified by preparative thin-layer chromatography
  8. dissolutionThe obtained compound was dissolved in 1.5 mL of N,N-dimethylformamide
  9. addition14.2 mg of benzoic acid and 21.3 mg of 4-dimethylaminopyridine were added
  10. stirringstirred
  11. stirringto homogenize the solution, and 22.3 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride
  12. additionwas added
  13. stirringstirred overnight at room temperature
  14. additionThereto, water was added
  15. extractionthe mixture was extracted with chloroform
  16. washThe organic layer was washed with saturated brine
  17. dry with materialdried over anhydrous sodium sulfate
  18. filtrationThe insolubles were filtered
  19. concentrationthe filtrate was concentrated under reduced pressure
  20. customthe thus obtained residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-b5f4d074919541e98399c70cee191cf5
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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