Sodium Hydroxide → [2-(4-Bromo-2-fluoro-benzylcarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid

HRID 457973ノート

反応式

HRID 457973 の反応式
C([O:3][C:4](=[O:27])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([CH3:14])=[CH:9][C:8]=1[C:15](=[O:26])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1[F:25])C.[OH-].[Na+]>C(O)C>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][NH:16][C:15]([C:8]2[CH:9]=[C:10]([CH3:14])[C:11]([F:13])=[CH:12][C:7]=2[O:6][CH2:5][C:4]([OH:27])=[O:3])=[O:26])=[C:19]([F:25])[CH:20]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 22093479(2-(4-Bromo-2-fluoro-benzylcarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid ethyl ester

生成物 1

HCID 22093452[2-(4-Bromo-2-fluoro-benzylcarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid収率 98.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A stirring solution of [2-(4-bromo-2-fluoro-benzylcarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid ethyl ester (0.72 g, 1.62 mmol) in ethanol (8.1 mL, 0.2 M) was placed in an ice bath and treated with aq NaOH (1.25 M, 7.8 mL, 9.73 mmol). The mixture was gradually allowed to warm to room temperature and after two hours the mixture was concentrated under reduced pressure, diluted with ethyl acetate, and treated with 2 N HCl (10 mL). The separated organic layer was washed with saturated aq NaCl. The organic layer was dried over Na2SO4, filtered, and concentrated to afford [2-(4-bromo-2-fluoro-benzylcarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid (0.66 g, 98%) as a white solid: mp 169° C.; Rf 0.22 (20% methanol in dichloromethane); 1H NMR (DMSO-d6, 0.300 MHz) δ 9.00 (bd t, J=5.3 Hz, 1 H), 7.76 (d, J=9.6 Hz, 1 H), 7.49 (d, J=9.6 Hz, 1 H), 7.39–7.33 (m, 2 H), 7.04 (dd, J1=11.4 Hz, J2=1.4 Hz, 1 H), 4.84 (d, J=1.8 Hz, 2 H), 4.48 (bd 8, 2 H), 2.17 (s, 3 H); ESI-LC/MS m/z calcd for C17H14BrF2NO4: 413.0; found 412 (M−1)−. Anal. calcd for C17H14BrF2NO4: C, 49.30; H, 3.41; N, 3.38. Found C, 49.32; H, 3.43; Br, 3.32.

後処理

  1. concentrationwas concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. additiontreated with 2 N HCl (10 mL)
  4. washThe separated organic layer was washed with saturated aq NaCl
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-da000b9fc32b4568ac6cd140c09943fa
出典データセット
uspto-grants-2007_03
特許番号
US07189749B2

反応ノート

読み込み中…