Tetrabutylammonium Fluoride → HCID 59279453, compound

HRID 1098144Notes

Reaction equation

HRID 1098144 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C@@H:27]([CH2:38][O:39][CH:40]1[CH2:43][CH2:42][CH2:41]1)[C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][N:32]=1)=[O:29])(C(C)(C)C)(C)C>O1CCCC1>[CH:40]1([O:39][CH2:38][C@H:27]([OH:26])[C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][N:32]=2)=[O:29])[CH2:41][CH2:42][CH2:43]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59279471HCID 59279471, compound2×

Product 1

HCID 59279453HCID 59279453, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tetrabutylammonium fluoride (1M in THF) (0.439 mL, 0.44 mmol) was added to a stirred solution of (S)-2-(tert-butyldimethylsilyloxy)-3-cyclobutoxy-N-(5-methylpyridin-2-yl)propanamide (Intermediate R5) (80 mg, 0.22 mmol) in tetrahydrofuran (5 mL). The resulting solution was stirred at room temperature for 4 hours. The reaction mixture was concentrated and diluted with ethyl acetate (20 mL) and washed sequentially with water (5 mL) and saturated brine (5 mL). The organic layer was dried (MgSO4) and evaporated. The crude product was purified by flash silica chromatography, eluting with 0 to 60% ethyl acetate in isohexane to afford the product (46.0 mg, 84%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate (20 mL)
  3. washwashed sequentially with water (5 mL) and saturated brine (5 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customThe crude product was purified by flash silica chromatography
  7. washeluting with 0 to 60% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-c46996efc42d45c1ba7fa80cc70a3db3
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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