Diisopropylamine → Tert-butyl 2-pivaloylamino-beta-hydroxy-beta-phenyl-3-pyridinepropanoate

HRID 398830Notes

Reaction equation

HRID 398830 reaction equation
CCCCCC.C([Li])CCC.C(NC(C)C)(C)C.[C:19]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:21])[CH3:20].[C:27]([C:35]1[C:36]([NH:41][C:42](=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44])=[N:37][CH:38]=[CH:39][CH:40]=1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O.O1CCCC1.CCOCC>[C:42]([NH:41][C:36]1[C:35]([C:27]([OH:34])([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:20][C:19]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:40][CH:39]=[CH:38][N:37]=1)(=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 10908tert-Butyl acetateHCID 14849372-Pivaloylamino-3-benzoylpyridineHCID 178418244HCID 178418244, compound

Product 1

HCID 10971347Tert-butyl 2-pivaloylamino-beta-hydroxy-beta-phenyl-3-pyridinepropanoateYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

In an atmosphere of argon, 1.69M n-butyl lithiumhexane solution (53 ml, 90.0 mmol) was added dropwise to an ether solution (150 ml) of diisopropylamine (9.61 g, 95.0 mmol) which was cooled at -78° C. After 15 minutes of stirring, an ether solution (20 ml) of tert-butyl acetate (10.5 g, 90.5 mmol) was slowly added dropwise. After 30 minutes of stirring, a tetrahydrofuran solution (30 ml) of 3-benzoyl-2-pivaloylaminopyridine (12.0 g, 42.6 mmol) was added dropwise. After 30 minutes of stirring, this was warmed up to room temperature and stirred for 5 hours. The reaction solution was poured into water and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration, the resulting filtrate was concentrated under reduced pressure to give tert-butyl 2-pivaloylamino-β-hydroxy-β-phenyl-3-pyridinepropanoate (16.9 g, 100%).

Workup

  1. stirringAfter 30 minutes of stirring
  2. stirringAfter 30 minutes of stirring
  3. temperaturethis was warmed up to room temperature
  4. stirringstirred for 5 hours
  5. extractionextracted with chloroform
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customAfter removing magnesium sulfate
  8. filtrationby filtration
  9. concentrationthe resulting filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-257a337bca244a18a3188787ba06967a
Source dataset
uspto-grants-1998_10
Patent number
US05817670

Reaction notes

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