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

HRID 19412ノート

反応式

HRID 19412 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

4

反応物 2

HCID 3939Lithium HydroxideHCID 66895190(R)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid ethyl ester

生成物 1

HCID 67486002(R)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid収率 98%

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 (R)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid ethyl ester (1.25 g, 3.42 mmol) in tetrahydrofuran (14 mL) was treated with a 0.5N lithium hydroxide solution (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 washed with diethyl ether. The organic phase was discarded and the aqueous layer acidified with 1N aqueous hydrochloric acid (10 mL) and extracted with ethyl acetate. The combined ethyl acetate layers were concentrated in vacuo which afforded (R)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid (1.13 g, 98%) as a pale brown solid.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water (40 mL)
  3. washwashed 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-22b8b902fbc346e48fdc89b7741c4918
出典データセット
uspto-grants-2010_06
特許番号
US07741327B2

反応ノート

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