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

HRID 457973노트

반응식

HRID 457973 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-da000b9fc32b4568ac6cd140c09943fa
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189749B2

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