Ethyl bromoacetate → Ethyl {(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazine-1-yl}acetate

HRID 1061672Notes

Reaction equation

HRID 1061672 reaction equation
[H-].[Na+].[C:3]([N:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:9][C:8](=[O:18])[CH:7]1[CH:19]([CH3:21])[CH3:20])(=[O:5])[CH3:4].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[C:3]([N:6]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:9]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:8](=[O:18])[CH:7]1[CH:19]([CH3:21])[CH3:20])(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22284395(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazine

Product 1

HCID 21302833Ethyl {(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazine-1-yl}acetate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under ice cooling, 60% sodium hydride (27.9 mg) is added to a solution of (3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazine (150 mg, Reference compound No. 49-1) in tetrahydrofuran (1 ml), and the mixture is stirred for 30 minutes. Ethyl bromoacetate (77 μl) is added to the mixture, then the temperature is raised to room temperature, and the whole is stirred for one hour. The reaction mixture is diluted with ethyl acetate, and a saturated aqueous ammonium chloride solution is added thereto. The diluted solution is washed with 0.1 N hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and saturated brine successively and dried over anhydrous magnesium sulfate. The diluted solution is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled reference compound (195 mg).

Workup

  1. washThe diluted solution is washed with 0.1 N hydrochloric acid
  2. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated brine successively and dried over anhydrous magnesium sulfate
  3. concentrationThe diluted solution is concentrated under reduced pressure
  4. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ed90c8f2eef7405bbb566cf3c56ac4f8
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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