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Lithium Hydroxide → (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid

HRID 19408
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인쇄 미리보기

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HRID 19408 반응식
C([O:3][C:4](=[O:25])[C@@H:5]([N:11]1[CH2:15][C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:13][C:12]1=[O:24])[CH2:6][CH:7]([CH3:10])[CH2:8][CH3:9])C.[OH-].[Li+]>O1CCCC1>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[O:16][C:14]1[CH2:15][N:11]([C@@H:5]([CH2:6][CH:7]([CH3:10])[CH2:8][CH3:9])[C:4]([OH:25])=[O:3])[C:12](=[O:24])[CH:13]=1
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참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 66894874(S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid ethyl ester

생성물 1

HCID 66894966(S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid수율 96%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
5 °C

실험 절차

A solution of (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid ethyl ester (0.95 g, 2.60 mmol) in tetrahydrofuran (15 mL) was treated with an aqueous 0.5N lithium hydroxide solution (10.4 mL) and stirred at 5° C. for 2 h. The mixture was concentrated in vacuo and the residue was dissolved in water (40 mL) and extracted with diethyl ether. The ether layer was discarded, and the aqueous layer was acidified with 1N aqueous hydrochloric acid (8 mL) and extracted with ethyl acetate. The combined ethyl acetate layers were concentrated in vacuo which afforded (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid (839 mg, 96%) as a pale orange solid.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water (40 mL)
  3. extractionextracted with diethyl ether
  4. extractionextracted with ethyl acetate
  5. concentrationThe combined ethyl acetate layers were concentrated in vacuo which

출처 및 근거

ORD 기록
ord-b8ff6db2dcd5462eb611bb67c011f788
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07741327B2

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