Tetrabutylammonium Fluoride → HCID 59063640, compound

HRID 49404Notes

Reaction equation

HRID 49404 reaction equation
C([Si](C)(C)[O:6][C@H:7]([C:25]1[CH:26]=[CH:27][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[N:29][CH:30]=1)[CH2:8][NH:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]([CH3:24])[S:22][CH:23]=2)=[CH:15][CH:14]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:6][C@H:7]([C:25]1[CH:26]=[CH:27][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[N:29][CH:30]=1)[CH2:8][NH:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:20]=[C:21]([CH3:24])[S:22][CH:23]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69743740(R)-N-[5-(1-(tert-Butyl-dimethyl-silanyloxy)-2-{2-[4-(2-methyl-thiazol-4-yl)-phenoxy]-ethylamino}-ethyl)-pyridin-2-yl]-acetamide

Product 1

HCID 59063640HCID 59063640, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-N-[5-(1-(tert-butyl-dimethyl-silanyloxy)-2-{2-[4-(2-methyl-thiazol-4-yl)-phenoxy]-ethylamino}-ethyl)-pyridin-2-yl]-acetamide (115 mg, 0.218 mmol) in tetrahydrofuran (1.5 mL) was added tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 0.65 mL, 0.65 mmol) at room temperature. The resulting solution was allowed to stir for about two and one-half hours, and the reaction mixture was then partitioned between ethyl acetate and water. The pH of the mixture was adjusted to about 10-11, and the aqueous phase was then extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude material was purified by column chromatography (methylene chloride to 20% methanol/methylene chloride) to afford 75 mg (83%) of the desired product. LRMS ([M+1]+): 413.2.

Workup

  1. customthe reaction mixture was then partitioned between ethyl acetate and water
  2. extractionthe aqueous phase was then extracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude material was purified by column chromatography (methylene chloride to 20% methanol/methylene chloride)

Sources & evidence

ORD record
ord-c23a80a61b884a94a1b5a7f2d30b582e
Source dataset
uspto-grants-2004_03
Patent number
US06706743B2

Reaction notes

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