Sodium Hydroxide → HCID 60073834, compound

HRID 1061690Notes

Reaction equation

HRID 1061690 reaction equation
[OH-].[Na+].[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]([NH:21][C@@H:22]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:23]([O:25]C)=[O:24])=[O:20])[C:8](=[O:34])[CH:7]1[CH:35]([CH3:37])[CH3:36])(=[O:5])[CH3:4]>C(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]([CH2:18][C:19]([NH:21][C@@H:22]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:23]([OH:25])=[O:24])=[O:20])[C:8](=[O:34])[CH:7]1[CH:35]([CH3:37])[CH3:36])(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86759893HCID 86759893, compound

Product 1

HCID 60073834HCID 60073834, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 4 N aqueous sodium hydroxide solution (7.2 ml) is added to a solution of methyl (2S)-2-{(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-3-phenylpropionate (4.60 g, Compound No. 1-48) in ethanol (30 ml), and the mixture is stirred for 4.5 hours. The reaction mixture is washed with ether, then 2 N hydrochloric acid is added to the reaction mixture 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 compound (4.46 g).

Workup

  1. washThe reaction mixture is washed with ether
  2. addition2 N hydrochloric acid is added to the reaction mixture
  3. extractionthe whole is extracted with ethyl acetate
  4. washThe extract is washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe extract is concentrated under reduced pressure

Sources & evidence

ORD record
ord-4695e352412140cab7c8bec6c2768901
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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