Tetrabutylammonium Fluoride → 7-[[4-(1-Hydroxyhexyl)benzyl]methanesulfonylamino]heptanoic Acid Ethyl Ester

HRID 606547Notes

Reaction equation

HRID 606547 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:21][C:22](=[O:55])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][S:30]([CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([CH:41]([O:47][Si](C(C)(C)C)(C)C)[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[CH:37][CH:36]=1)(=[O:32])=[O:31])[CH3:20]>C1COCC1.CCOC(C)=O>[CH2:19]([O:21][C:22](=[O:55])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][S:30]([CH2:33][CH2:34][C:35]1[CH:36]=[CH:37][C:38]([CH:41]([OH:47])[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[CH:39][CH:40]=1)(=[O:31])=[O:32])[CH3:20]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 670466937-[[4-(1-(tert-Butyldimethylsilanyloxy)hexyl)benzyl]methanesulfonylamino]-heptanoic Acid Ethyl Ester

Product 1

HCID 670459707-[[4-(1-Hydroxyhexyl)benzyl]methanesulfonylamino]heptanoic Acid Ethyl EsterYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Tetrabutylammonium fluoride (0.6 mL of a 1.0 M solution in THF, 0.6 mmol) was added to a solution of the silylether 10 (159 mg, 0.29 mmol) in THF (3.0 mL) at 23° C. The reaction was stirred for 16 h, diluted with EtOAc and washed with water. The organic portion was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 2:1 hex/EtOAc) afforded 118.6 mg (94%) of the alcohol 11 as a light yellow, viscous oil.

Workup

  1. washwashed with water
  2. washThe organic portion was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5514a5ab3d143388fb59fcd064441e6
Source dataset
uspto-grants-2011_03
Patent number
US07915316B2

Reaction notes

Loading…