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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
ノート
印刷プレビュー

反応式

HRID 19408 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b8ff6db2dcd5462eb611bb67c011f788
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07741327B2

反応ノート

読み込み中…

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