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

HRID 457975노트

반응식

HRID 457975 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](=[S: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])=[S:26])=[C:19]([F:25])[CH:20]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 22093484[2-(4-Bromo-2-fluoro-benzylthiocarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid ethyl ester

생성물 1

HCID 22093458[2-(4-Bromo-2-fluoro-benzylthiocarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid수율 98.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A stirring solution of [2-(4-bromo-2-fluoro-benzylthiocarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid ethyl ester (0.79 g, 1.53 mmol) in ethanol (7.6 mL, 0.2 M) and treated with aqueous NaOH (2 N, 7.4 mL, 9.15 mmol) in an analogous fashion to Example 45, Step 9 to provide [2-(4-bromo-2-fluoro-benzylthiocarbamoyl)-5-fluoro-4-methyl-phenoxy]-acetic acid (0.65 g, 98%) as a yellow solid: mp 162–164° C.; Rf 0.41 (20% methanol in methylene chloride); 1H NMR (DMSO-d6, 300 mHz) δ 10.64 (t, J=5.0 Hz, 1 H), 7.61 (d, J=9.0 Hz, 1 H), 7.52 (dd, J1=9.6 Hz, J2=1.7 Hz, 1 H), 7.45–7.36 (m, 2 H), 7.00 (d, J=11.4 Hz, 1 H), 4.89 (bd d, J=5.1 Hz, 2 H), 4.78 (s, 2 H), 2.15 (d, J=1.2 Hz, 3 H); ESI-LC/MS m/z calcd for C17H14BrF2NO3S: 428.98; found 428.0 (M−1)−; Anal. calcd for C17H14BrF2NO3S: C, 47.45; H, 3.28; N, 3.26; S, 7.45. Found C, 47.54; H, 3.19; N, 3.11; S, 7.33.

출처 및 근거

ORD 기록
ord-01c4f62ab8a14209bf1909f8156b784c
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189749B2

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