Water → HCID 69384373, compound

HRID 916827Notes

Reaction equation

HRID 916827 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][CH2:18][C@@H:19]([C:21]2[CH:32]=[CH:31][C:24]3[O:25][C:26]([CH3:30])([CH3:29])[O:27][CH2:28][C:23]=3[CH:22]=2)[OH:20])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[C:33](N1C=CN=C1)(N1C=CN=C1)=[O:34].O>C1COCC1>[CH3:30][C:26]1([CH3:29])[O:25][C:24]2[CH:31]=[CH:32][C:21]([C@H:19]3[O:20][C:33](=[O:34])[N:17]([CH2:16][CH2:15][C:12]4[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=4)[CH2:18]3)=[CH:22][C:23]=2[CH2:28][O:27]1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 69386381(1R)-2-{[2-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)ethyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol

Product 1

HCID 69384373HCID 69384373, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (1R)-2-{[2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethyl]amino}-1-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)ethanol (4.803 g) in THF (100 ml) under nitrogen was treated with 1,1′carbonyldimidazole (1.702 g) and the mixture was stirred at 20° for 21.5 h. Water (125 ml) was added, the mixture was stirred for 10 min and then extracted with Et2O. The extract was dried (Na2SO4) and the solvent evaporated in vacuo. The residue was dissolved in THF (60 ml) and was treated with a solution of tetrabutyl ammonium fluoride in THF (1.0 M, 15.95 ml). The mixture was stirred at 20° for 100 min, water (30 ml) was added and the mixture was extracted with Et2O. The extract was washed with water, dried (Na2SO4) and the solvent evaporated in vacuo to give a residue which was purified by chromatography on a Biotage cartridge (90 g). Elution with EtOAc-petroleum ether (2:3) gave the title compound (2.82 g). LCMS RT=3.01 min ES+ve 370 (MH)+.

Workup

  1. stirringthe mixture was stirred for 10 min
  2. extractionextracted with Et2O
  3. dry with materialThe extract was dried (Na2SO4)
  4. customthe solvent evaporated in vacuo
  5. dissolutionThe residue was dissolved in THF (60 ml)
  6. additionwas treated with a solution of tetrabutyl ammonium fluoride in THF (1.0 M, 15.95 ml)
  7. stirringThe mixture was stirred at 20° for 100 min
  8. additionwater (30 ml) was added
  9. extractionthe mixture was extracted with Et2O
  10. washThe extract was washed with water
  11. dry with materialdried (Na2SO4)
  12. customthe solvent evaporated in vacuo
  13. customto give a residue which
  14. customwas purified by chromatography on a Biotage cartridge (90 g)
  15. washElution with EtOAc-petroleum ether (2:3)

Sources & evidence

ORD record
ord-e13039714b054d848e3e263088ad3c99
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

Loading…