Hydrochloric Acid → [4-(2-Chlorophenyl)-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetic acid

HRID 2373714ノート

反応式

HRID 2373714 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:27][C:28]([O:30]C)=[O:29])=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([NH:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:20])=[CH:15][CH:14]=2)[S:11][CH:12]=1.[OH-].[Na+].Cl>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:27][C:28]([OH:30])=[O:29])=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([NH:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:20])=[CH:15][CH:14]=2)[S:11][CH:12]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86607183Methyl [4-(2-chlorophenyl)-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetate

生成物 1

HCID 69200552[4-(2-Chlorophenyl)-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetic acid収率 95.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Methyl [4-(2-chlorophenyl)-2-(4-{[( 1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetate (0.145 g, 0.328 mmol) was dissolved in EtOH (2 mL). NaOH (0.65 mL, 1N, 0.65 mmol) was added and the solution heated to reflux for 5 h. HCl (0.35 mL, 2N, 0.70 mmol) was added and the solvent removed. The mixture was partitioned between EtOAc and H2O. The EtOAc layer was dried (MgSO4) and the solvent removed to yield [4-(2-chlorophenyl)-2-(4-{[(1-ethylpropyl)amino]carbonyl}phenyl)thien-3-yl]acetic acid (0.138 g) as a white solid. mp 101-103° C. 1H NMR (500 MHz, DMSO-d6) δ: 0.88 (t, 6H, J=7.3 Hz), 1.50 (m, 2H), 1.55 (m, 2H), 3.42 (s, 2H), 3.82 (m, 1H), 7.35 (m, 1H), 7.42 (m, 3H), 7.58 (m, 3H), 7.96 (d, 2H, J=8.4 Hz), 8.11 (d, 1H, J=8.7 Hz). MS (ES) m/z 442.1 ([M+H]+). MS (ES) m/z 883.1 ([2M+H]+). Anal. Calcd for C24H24ClNO3S: C, 65.22; H, 5.47; N, 3.17. Found: C, 62.33; H, 5.54; N, 3.01.

後処理

  1. temperaturethe solution heated
  2. temperatureto reflux for 5 h
  3. customthe solvent removed
  4. customThe mixture was partitioned between EtOAc and H2O
  5. dry with materialThe EtOAc layer was dried (MgSO4)
  6. customthe solvent removed

出典と根拠

ORDレコード
ord-391e51f0da5f4e2a8ed15adf550e0229
出典データセット
uspto-grants-2008_12
特許番号
US07459567B2

反応ノート

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