Sodium Hydroxide → HCID 11359833, compound

HRID 1269400Notes

Reaction equation

HRID 1269400 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-95bf4f07b6254689b5c5e1ce1fd468be
Source dataset
uspto-grants-2007_04
Patent number
US07199150B2

Reaction notes

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