Methanol → [2-difluoromethoxy-8-fluoro-3-(4-fluorobenzyl)-4-methylquinolin-5-yloxy]acetic Acid

HRID 2266557ノート

反応式

HRID 2266557 の反応式
C[O:2][C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([CH3:29])=[C:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[C:10]([O:17][CH:18]([F:20])[F:19])=[N:11]2.O1CCCC1.CO.[OH-].[Li+]>O>[F:20][CH:18]([F:19])[O:17][C:10]1[C:9]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)=[C:8]([CH3:29])[C:7]2[C:12](=[C:13]([F:16])[CH:14]=[CH:15][C:6]=2[O:5][CH2:4][C:3]([OH:30])=[O:2])[N:11]=1

参加物

6

反応物 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68786070[2-difluoromethoxy-8-fluoro-3-(4-fluorobenzyl)-4-methylquinolin-5-yloxy]acetic Acid Methyl Ester

生成物 1

HCID 57742512[2-difluoromethoxy-8-fluoro-3-(4-fluorobenzyl)-4-methylquinolin-5-yloxy]acetic Acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of [2-difluoromethoxy-8-fluoro-3-(4-fluorobenzyl)-4-methylquinolin-5-yloxy]acetic acid methyl ester (0.20 g), tetrahydrofuran (4.0 mL), methanol (4.0 mL), water (3.0 mL) and lithium hydroxide (0.020 g) was stirred at room temperature for 40 minutes. The mixture was partitioned between ethyl acetate and 1.0 M aqueous hydrochloric acid. The aqueous phase was extracted with ethyl acetate and the combined organic phases were dried over sodium sulfate and the solvent removed under reduced pressure. Purification of the residue by preparative reverse-phase HPLC using a gradient over 30 minutes of acetonitrile in water gave title compound as a white solid, 0.10 g.

後処理

  1. customThe mixture was partitioned between ethyl acetate and 1.0 M aqueous hydrochloric acid
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined organic phases were dried over sodium sulfate
  4. customthe solvent removed under reduced pressure
  5. customPurification of the residue by preparative reverse-phase
  6. customover 30 minutes

出典と根拠

ORDレコード
ord-1303acc1dcdd4731a2c050f9708a754c
出典データセット
uspto-grants-2010_12
特許番号
US07858640B2

反応ノート

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