Tetrabutylammonium Fluoride → HCID 86707345, compound

HRID 239962Notes

Reaction equation

HRID 239962 reaction equation
[Si]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[N:21]=[C:20]([C:22]([NH:24][C:25]3[C:34]([CH3:35])=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][C:26]=3[CH3:36])=[O:23])[C:19]([CH3:37])=[CH:18][CH:17]=2)[CH2:11]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[N:21]=[C:20]([C:22]([NH:24][C:25]3[C:26]([CH3:36])=[CH:27][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:33][C:34]=3[CH3:35])=[O:23])[C:19]([CH3:37])=[CH:18][CH:17]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86707346HCID 86707346, compound

Product 1

HCID 86707345HCID 86707345, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 4-[[6-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoate (0.22 g, 0.873 mmol) in THF (3 ml) is added Bu4NF 1.0 M in THF (2.00 ml) at 0° C. The reaction mixture is gradually warmed to ambient temperature. After 8 hours, the reaction mixture is diluted with ice-water and extracted twice with ethyl acetate. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by flash chromatography (silica gel) over a gradient using 0-40% ethyl acetate in hexanes to afford the title compound as a white solid (0.06 g, 30%). Mass spectrum (m/z): 412.2 (M+1).

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a residue
  6. customThe residue is purified by flash chromatography (silica gel) over a gradient

Sources & evidence

ORD record
ord-da4c12890c3f4a8db71e52386299f3f9
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

Loading…