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

HRID 860368

反応式

HRID 860368 の反応式
[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

参加物

4

反応物 3

HCID 6287L-ValineHCID 7679Phenylacetyl chlorideHCID 14798Sodium Hydroxide

生成物 1

HCID 853958(2S)-3-methyl-2-(2-phenylacetamido)butanoic acid収率 75%

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-737ff0ee57b0407dafaed4ccb01478f6
出典データセット
uspto-grants-2006_12
特許番号
US07153847B2

関連ノート

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