Water → HCID 69748332, compound

HRID 1061688Notes

Reaction equation

HRID 1061688 reaction equation
O.[OH-].[Li+].[C:4]([N:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]([CH2:19][C:20]([NH:22][C@@H:23]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:24](=[O:31])[C:25]([O:27]C(C)C)=[O:26])=[O:21])[C:9](=[O:39])[C@H:8]1[CH:40]([CH3:42])[CH3:41])(=[O:6])[CH3:5]>CO>[C:4]([N:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]([CH2:19][C:20]([NH:22][C@@H:23]([CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:24](=[O:31])[C:25]([OH:27])=[O:26])=[O:21])[C:9](=[O:39])[C@H:8]1[CH:40]([CH3:42])[CH3:41])(=[O:6])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86759892HCID 86759892, compound

Product 1

HCID 69748332HCID 69748332, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Water (0.45 ml) and a 1 N aqueous lithium hydroxide solution (55 μl) are added to a solution of isopropyl (3S)-3-{(3R)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-2-oxo-4-phenylbutyrate (24.5 mg, Compound No. 2-2) in methanol (0.5 ml), and the mixture is stirred for one hour. The reaction mixture is concentrated under reduced pressure, and 1 N hydrochloric acid is added to the concentrate to acidify the system. The whole is extracted with ethyl acetate, and the extract is washed with water and a saturated aqueous sodium hydrogencarbonate solution successively and dried over magnesium sulfate. The extract is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled compound (21.8 mg).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure, and 1 N hydrochloric acid
  2. additionis added to the
  3. concentrationconcentrate
  4. extractionThe whole is extracted with ethyl acetate
  5. washthe extract is washed with water
  6. dry with materiala saturated aqueous sodium hydrogencarbonate solution successively and dried over magnesium sulfate
  7. concentrationThe extract is concentrated under reduced pressure
  8. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-977837788d324188963fd0790b5130a7
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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