tert-Butyl acetate → HCID 68161930, compound

HRID 1892251Notes

Reaction equation

HRID 1892251 reaction equation
[Li+].CC([N-]C(C)C)C.[C:9]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])[CH3:10].[C:17]([C:20]1[C:21]([NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])=[N:22][CH:23]=[CH:24][CH:25]=1)(=[O:19])[CH3:18]>C1COCC1>[OH:19][C:17]([C:20]1[C:21]([NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])=[N:22][CH:23]=[CH:24][CH:25]=1)([CH3:18])[CH2:10][C:9]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 10908tert-Butyl acetateHCID 2724682Lithium diisopropylamideHCID 19354338HCID 19354338, compound

Product 1

HCID 68161930HCID 68161930, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 9.5 mL (2.1 eq) of LDA in 15 mL THF at −78° C. was added 2.0 mL of t-butyl acetate (2.1 eq.). The resulting mixture was stirred at −78° C. for 30 minutes after which a solution of N-(3-acetylpyridin-2-yl)pivalamide (1.52 g, 6.90 mmol) in THF was added in a dropwise fashion. The resulting reaction mixture was then stirred at −78° C. for 30 minutes and was brought up to room temperature. The reaction mixture was then quenched with saturated NH4Cl. The resulting mixture was extracted with EtOAc (3×20 mL) and the combined organic extracts were washed with H2O (2×20 mL), brine (1×20 mL), dried over MgSO4 and concentrated to give the title compound (1.40 g, 61%). Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 1.33 (s, 9 H) 1.44 (s, 9 H) 1.58 (s, 3 H) 2.65 (d, J=16.70 Hz, 1 H) 3.06 (d, J=16.70 Hz, 1 H) 5.54 (s, 1 H) 6.96 (dd, J=7.76, 4.83 Hz, 1 H) 7.43 (dd, J=7.91, 1.76 Hz, 1 H) 8.45 (dd, J=4.98, 1.76 Hz, 1 H) 10.29 (s, 1 H).

Workup

  1. additionwas added in a dropwise fashion
  2. customThe resulting reaction mixture
  3. customwas brought up to room temperature
  4. customThe reaction mixture was then quenched with saturated NH4Cl
  5. extractionThe resulting mixture was extracted with EtOAc (3×20 mL)
  6. washthe combined organic extracts were washed with H2O (2×20 mL), brine (1×20 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-434345c01e36488db902df8e7fd3dc9b
Source dataset
uspto-grants-2013_08
Patent number
US08507682B2

Reaction notes

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