Tetrabutylammonium Fluoride → HCID 67122860, compound

HRID 1802428Notes

Reaction equation

HRID 1802428 reaction equation
[CH3:1][C:2]([C:16]1[O:20][N:19]=[C:18]([NH:21][C:22](=[O:37])[C:23]([CH3:36])([S:25]([CH2:28][CH2:29][CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)(=[O:27])=[O:26])[CH3:24])[CH:17]=1)([CH3:15])[CH2:3][O:4][Si](C(C)C)(C(C)C)C(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.[NH4+].[Cl-]>[OH:4][CH2:3][C:2]([C:16]1[O:20][N:19]=[C:18]([NH:21][C:22](=[O:37])[C:23]([CH3:24])([S:25]([CH2:28][CH2:29][CH:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)(=[O:27])=[O:26])[CH3:36])[CH:17]=1)([CH3:15])[CH3:1]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67122941HCID 67122941, compound

Product 1

HCID 67122860HCID 67122860, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 190 mg (0.34 mmol) of N-[5-(1,1-dimethyl-2-triisopropylsilanyloxy-ethyl)-isoxazol-3-yl]-2-methyl-2-[2-(tetrahydro-pyran-4-yl)-ethanesulfonyl]-propionamide in THF (2 mL) are added 1.7 mL (1M solution in THF, 1.7 mmol) of tetrabutylammonium fluoride. The reaction is stirred at room temperature for 18 h and then diluted with 1M aqueous NH4Cl solution (5 mL). The aqueous layer is extracted with DCM (3×25 mL). The combined organic extracts are dried over Na2SO4 and filtered and the filtrate concentrated under reduced pressure to give 46 mg of N-[5-(2-hydroxy-1,1-dimethyl-ethyl)-isoxazol-3-yl]-2-methyl-2-[2-(tetrahydro-pyran-4-yl)-ethanesulfonyl]-propionamide. Yield: 34%, ES-MS: m/z 403 [M+H]

Workup

  1. extractionThe aqueous layer is extracted with DCM (3×25 mL)
  2. dry with materialThe combined organic extracts are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-68e8818936a146d19dd5b26fe754dc37
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

Loading…