L-Valine → N-(phenylacetyl)valine 2-methylbutyl Ester

HRID 1841162Notes

Reaction equation

HRID 1841162 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[OH-].[Na+].[C:11]1([CH2:17][C:18](Cl)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH3:4][CH:3]([CH2:2][CH3:6])[CH2:5][O:7][C:6](=[O:8])[C@H:2]([CH:3]([CH3:5])[CH3:4])[NH:1][C:18](=[O:19])[CH2:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 6287L-ValineHCID 7679Phenylacetyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 15481773N-(phenylacetyl)valine 2-methylbutyl EsterYield 136.4%

Procedure

To a stirred solution of 5.15 g (44 mmol) of valine (Bachem) in 50 mL (100 mmol) of 2N NaOH cooled to 0° C. was added dropwise 5.3 mL (40 mmol) of phenylacetyl chloride (Aldrich). A colorless oil precipitated. The reaction mixture was allowed to warm to room temperature and stirred for 18 hours, washed with 50 mL diethyl ether, acidified to pH 2-3 with aqueous HCl. The white precipitate formed was filtered off, washed thoroughly with water, followed by diethyl ether to give 7.1 g (30 mmol, 69% yield) of the title compound.

Workup

  1. customA colorless oil precipitated
  2. washwashed with 50 mL diethyl ether
  3. customThe white precipitate formed
  4. filtrationwas filtered off
  5. washwashed thoroughly with water

Sources & evidence

ORD record
ord-e478c4f0e3c44b23a55f5929d67fef5a
Source dataset
uspto-grants-2004_01
Patent number
US06683075B1

Reaction notes

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