Sodium Hydroxide → HCID 11359833, compound

HRID 1869664Notes

Reaction equation

HRID 1869664 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-86ba536a0f354619adb4e1c27c43d51b
Source dataset
uspto-grants-2009_12
Patent number
US07638551B2

Reaction notes

Loading…