Hydrochloric Acid → (2-(4-Bromo-2-fluoro-benzylcarbamoyl)-5-methoxy-phenoxy]-acetic acid

HRID 2229533ノート

反応式

HRID 2229533 の反応式
C([O:3][C:4](=[O:26])[CH2:5][O:6][C:7]1[CH:12]=[C:11](Cl)[CH:10]=[CH:9][C:8]=1[C:14](=[O:25])[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=1[F:24])C.[OH-].[Na+].Cl.[CH2:30]([OH:32])C>C(OCC)(=O)C>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][NH:15][C:14]([C:8]2[CH:9]=[CH:10][C:11]([O:32][CH3:30])=[CH:12][C:7]=2[O:6][CH2:5][C:4]([OH:3])=[O:26])=[O:25])=[C:18]([F:24])[CH:19]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 22093478[2-(4-Bromo-2-fluoro-benzylcarbamoyl)-5-chloro-phenoxy]-acetic acid ethyl ester

生成物 1

HCID 22093455(2-(4-Bromo-2-fluoro-benzylcarbamoyl)-5-methoxy-phenoxy]-acetic acid収率 89%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A solution of [2-(4-bromo-2-fluoro-benzylcarbamoyl)-5-chloro-phenoxy]-acetic acid ethyl ester (1.23 g, 2.8 mmol) in ethanol (16 mL, 0.18 M) was cooled to 0° C. and treated with aq NaOH (1.25 M, 7.0 mL, 8.7 mmol). After stirring for 2.5 h, the solution was warmed to room temperature and stirred an additional 24 h. Next, the solution was acidified to pH 1-2 with 2 N HCl, diluted with ethyl acetate and washed with saturated aq NaCl. The organic layer was dried over Na2SO4, filtered and concentrated to give [2-(4-bromo-2-fluoro-benzylcarbamoyl)-5-methoxy-phenoxy]-acetic acid as a white solid (1.03 g, 89%): mp 203-204° C.; Rf 0.10 (10% methanol in dichloromethane); 1H NMR (DMSO-d6, 300 MHz) δ 9.02 (br t, J=5.9 Hz, 1H), 7.84, (d, J=8.2 Hz, 1H), 7.50, (br d, J=8.7 Hz, 1H), 7.48-7.29 (m, 2H), 6.69-6.8 0 (m, 2H), 4.87 (s, 2H), 4.49 (d, J=5.8 Hz, 2H), 3.79 (s, 3H). ESI-LC/MS m/z calcd for C17H15BrFNO5: 411.0; found 412.0 (M+1)−. Anal. calcd for C17H15BrFNO5: C, 49.53; H, 3.67; N, 3.40. Found C, 49.48; H, 3.68; N, 3.39.

後処理

  1. stirringstirred an additional 24 h
  2. washwashed with saturated aq NaCl
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-2eb08a1c914e4e3e855258a64457ac16
出典データセット
uspto-grants-2002_07
特許番号
US06420426B1

反応ノート

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