L-Valine → (2S)-3-methyl-2-(2-phenylacetamido)butanoic acid

HRID 2180735

Reaction equation

HRID 2180735 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>>[C:11]1([CH2:17][C:18]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])=[O:19])[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 853958(2S)-3-methyl-2-(2-phenylacetamido)butanoic acidYield 75%

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-4155c19f3e7548ed84d02b29d26f5a76
Source dataset
uspto-grants-2005_05
Patent number
US06888022B2

Linked notes

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