Sodium Hydroxide → HCID 11359833, compound

HRID 562623Notes

Reaction equation

HRID 562623 reaction equation
Cl.[NH2:2][C@:3]([CH3:26])([CH2:6][CH2:7][C:8]1[N:9]([CH3:25])[C:10]([C:13](=[O:24])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:11][CH:12]=1)[CH2:4][OH:5].[OH-].[Na+]>ClCCl>[NH2:2][C@:3]([CH3:26])([CH2:6][CH2:7][C:8]1[N:9]([CH3:25])[C:10]([C:13](=[O:24])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:11][CH:12]=1)[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66672923HCID 66672923, compound

Product 1

HCID 11359833HCID 11359833, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (2R)-2-amino-2-methyl-4-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]butan-1-ol hydrochloride (185 mg, 0.49 mmol) obtained in Example (33b) in dichloromethane (10 ml) was added 1N aqueous sodium hydroxide solution, and the resulting mixture was stirred for 5 minutes. After stirring, the reaction mixture was extracted with dichloromethane, and the extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo to afford (2R)-2-amino-2-methyl-4-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]butan-1-ol.

Workup

  1. stirringAfter stirring
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. washthe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-05fea13351bc4393b255f4f0fe428fd7
Source dataset
uspto-grants-2011_11
Patent number
US08067396B2

Reaction notes

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