Tetrabutylammonium Fluoride → HCID 86707356, compound

HRID 1427125Notes

Reaction equation

HRID 1427125 reaction equation
[Si]([O:8][CH2:9][CH:10]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[C:19]([C:21]([NH:23][C:24]3[C:33]([CH3:34])=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:25]=3[CH3:35])=[O:22])[C:18]([CH3:36])=[CH:17][CH:16]=2)[CH2:11]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][CH:10]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[C:19]([C:21]([NH:23][C:24]3[C:25]([CH3:35])=[CH:26][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:32][C:33]=3[CH3:34])=[O:22])[C:18]([CH3:36])=[CH:17][CH:16]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86707357HCID 86707357, compound

Product 1

HCID 86707356HCID 86707356, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 4-[[6-[3-[[tert-butyl(dimethyl) silyl]oxymethyl]pyrrolidin-1-yl]-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoate (1.1 g, 2.15 mmol) in THF (7 ml) is added Bu4NF 1.0 M in THF (5.00 ml) at 0° C. The reaction mixture is gradually warmed to ambient temperature. After 6 hours, the reaction mixture is diluted with ice-water and extracted with ethyl acetate. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (silica gel) over a gradient using 0-50% ethyl acetate in hexanes to afford the title compound as an off-white solid (0.36 g, 42%). Mass spectrum (m/z): 398.2 (M+1).

Workup

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

Sources & evidence

ORD record
ord-9aae07bae456456a80420018d4b1144d
Source dataset
uspto-grants-2015_01
Patent number
US08933098B2

Reaction notes

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