Hydrochloric Acid → {(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}acetic acid

HRID 1061673Notes

Reaction equation

HRID 1061673 reaction equation
[OH-].[Li+].[C:3]([N:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:9]([CH2:18][C:19]([O:21]CC)=[O:20])[C:8](=[O:24])[CH:7]1[CH:25]([CH3:27])[CH3:26])(=[O:5])[CH3:4].Cl>C(O)C>[C:3]([N:6]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:9]([CH2:18][C:19]([OH:21])=[O:20])[C:8](=[O:24])[CH:7]1[CH:25]([CH3:27])[CH3:26])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21302833Ethyl {(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazine-1-yl}acetate

Product 1

HCID 22284314{(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 4 N aqueous lithium hydroxide solution (0.4 ml) is added to a solution of ethyl {(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}acetate (185 mg, Reference compound No. 50-1) in ethanol (5 ml), and the mixture is stirred for 35 minutes. To the reaction mixture is added 1 N hydrochloric acid to acidify the system, and the whole is extracted with ethyl acetate. The extract is washed with saturated brine and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure to give the titled reference compound (167 mg).

Workup

  1. extractionthe whole is extracted with ethyl acetate
  2. washThe extract is washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe extract is concentrated under reduced pressure

Sources & evidence

ORD record
ord-dd6bc8da0bd54efdbad36ff9f2863d88
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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