Lithium hydroxide, monohydrate → (S)-2-{4-[4-(2-hydroxy-2-methyl-propyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid

HRID 19382ノート

反応式

HRID 19382 の反応式
C[O:2][C:3](=[O:27])[C@@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([OH:25])([CH3:24])[CH3:23])=[CH:17][CH:16]=2)=[CH:11][C:10]1=[O:26])[CH2:5][CH:6]([CH3:8])[CH3:7].O.[OH-].[Li+]>O1CCCC1.O>[OH:25][C:22]([CH3:24])([CH3:23])[CH2:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][C:12]2[CH2:13][N:9]([C@@H:4]([CH2:5][CH:6]([CH3:7])[CH3:8])[C:3]([OH:27])=[O:2])[C:10](=[O:26])[CH:11]=2)=[CH:20][CH:19]=1

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 66895035HCID 66895035、化合物

生成物 1

HCID 66895044(S)-2-{4-[4-(2-hydroxy-2-methyl-propyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid収率 83%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (S)-2-{4-[4-(2-hydroxy-2-methyl-propyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid methyl ester (0.150 g, 0.40 mmol) in tetrahydrofuran (5 mL) and water (1 mL) was treated with lithium hydroxide monohydrate (0.017 g 0.40 mmol). The mixture was stirred at room temperature for 1.75 h and then partitioned between ethyl acetate and water. The water layer was made acidic with 1N aqueous hydrochloric acid (pH=1) and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford (S)-2-{4-[4-(2-hydroxy-2-methyl-propyl)-phenoxy]-2-oxo-2,5-dihydro-pyrrol-1-yl}-4-methyl-pentanoic acid (0.120 g, 83%) as a white solid.

後処理

  1. custompartitioned between ethyl acetate and water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a1c989e098ee47898365bdf080662094
出典データセット
uspto-grants-2010_06
特許番号
US07741327B2

反応ノート

読み込み中…