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

HRID 860368

반응식

HRID 860368 반응식
[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

참가 물질

4

반응물 3

HCID 6287L-ValineHCID 7679Phenylacetyl chlorideHCID 14798Sodium Hydroxide

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-737ff0ee57b0407dafaed4ccb01478f6
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153847B2

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