Sodium Hydroxide → {5-Fluoro-2-[(3-Nitrobenzyl)carbamoyl]phenoxy}acetic Acid

HRID 457954ノート

反応式

HRID 457954 の反応式
C([O:3][C:4](=[O:27])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14](=[O:26])[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)C.[OH-].[Na+]>C(O)C>[F:13][C:11]1[CH:10]=[CH:9][C:8]([C:14](=[O:26])[NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)=[C:7]([CH:12]=1)[O:6][CH2:5][C:4]([OH:27])=[O:3]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 22093485[5-Fluoro-2-(3-nitro-benzylcarbamoyl)-phenoxy]-acetic acid ethyl ester

生成物 1

HCID 9798381{5-Fluoro-2-[(3-Nitrobenzyl)carbamoyl]phenoxy}acetic Acid収率 98.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A suspension of [5-fluoro-2-(3-nitro-benzylcarbamoyl)-phenoxy]-acetic acid ethyl ester (3.3 g, 8.77 mmol) in ethanol (40 mL) was treated with aq 2 N NaOH (24 mL, 47.8 mmol). After stirring for 4 h, the solution was concentrated in vacuo until most of the ethanol was removed, and the mixture was acidified to pH of 1 with 2 N HCl. After extracting with ethyl acetate, the organic layer was washed with saturated aq NaCl, dried over MgSO4 and concentrated to give [5-fluoro-2-(3-nitro-benzylcarbamoyl)-phenoxy]-acetic acid as an off-white solid (3.00 g, 98%): mp 148–151° C.; Rf 0.39 (20% methanol in dichloromethane); 1H NMR (DMSO-d6 300 MHz) δ 9.20 (t, J=6.3 Hz, 1 H) 8.18 (s, 1 H), 8.09 (dd, J1=7.2 Hz, J2=2.7 Hz, 1 H), 7.90 (dd, J1=8.7 Hz, J2=7.0 Hz, 1 H), 7.79 (d, J=7.5 Hz, 1 H), 7.61 (t, J=7.8 Hz, 1 H), 7.08 (dd, J1=10.8 Hz, J2=2.1 Hz, 1 H), 6.91 (dt, J1=8.7 Hz, J2=2.4 Hz, 1 H), 4.89 (s, 2 H), 4.62 (d, J=6 Hz, 2 H). ESI-LC/MS m/z calcd for C16H13FN2O6: 348.3; Found 347.0 (M−1)−. Anal. calcd for C16H13FN2O6: C, 55.18; H, 3.76; N, 8.04. Found C, 55.02; H, 3.79; N, 7.98.

後処理

  1. concentrationthe solution was concentrated in vacuo until most of the ethanol
  2. customwas removed
  3. extractionAfter extracting with ethyl acetate
  4. washthe organic layer was washed with saturated aq NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-57ca775d10d84d779b76a384bee12439
出典データセット
uspto-grants-2007_03
特許番号
US07189749B2

反応ノート

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