Lithium Hydroxide → [3-(2-Benzenesulfonylpyridin-3-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid

HRID 1944401

反応式

HRID 1944401 の反応式
C[O:2][C:3](=[O:32])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:15][C:16]2[C:17]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[N:18][CH:19]=[CH:20][CH:21]=2)=[C:6]1[CH3:31].[OH-].[Li+]>O1CCCC1>[C:25]1([S:22]([C:17]2[C:16]([CH2:15][C:7]3[C:8]4[C:13](=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=4)[N:5]([CH2:4][C:3]([OH:32])=[O:2])[C:6]=3[CH3:31])=[CH:21][CH:20]=[CH:19][N:18]=2)(=[O:24])=[O:23])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 67044945[3-(2-Benzenesulfonylpyridin-3-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester

生成物 1

HCID 59380586[3-(2-Benzenesulfonylpyridin-3-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid収率 70.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of [3-(2-benzenesulfonylpyridin-3-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester (0.16 g) and tetrahydrofuran (5.0 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.5 mL), and the resulting mixture was stirred at room temperature for 30 minutes. The mixture was concentrated under reduced pressure, pH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The combined organic extract was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (5:95 to 98:2 by volume) to afford the title compound as a white solid (0.11 g).

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionpH adjusted to 4 by the addition of 0.1 M aqueous hydrochloric acid solution
  3. extractionextracted with ethyl acetate
  4. extractionThe combined organic extract
  5. washwas washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by preparative reverse-phase HPLC
  9. washeluting with a mixture of acetonitrile and water (5:95 to 98:2 by volume)

出典と根拠

ORDレコード
ord-34eaa9904c9c424c84bb5be4faa2ef1c
出典データセット
uspto-grants-2013_03
特許番号
US08394836B2

関連ノート

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