octanedioic acid [4-(3-Nitro-phenyl)-thiazol-2-yl]-amide methyl ester → octanedioic acid [4-(3-Amino-phenyl)-thiazol-2-yl]-amide methyl ester

HRID 243625

反応式

HRID 243625 の反応式
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=2)[N:17]=1)=[O:11]>CCO.CC(O)=O.[Pd]>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][C:13]1[S:14][CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=2)[N:17]=1)=[O:11]

参加物

5

反応物 1

HCID 44550802octanedioic acid [4-(3-Nitro-phenyl)-thiazol-2-yl]-amide methyl ester

生成物 1

HCID 44550930octanedioic acid [4-(3-Amino-phenyl)-thiazol-2-yl]-amide methyl ester収率 72.4%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒

実験手順

A suspension of compound 14 (0.391 g, 1 mmol) and Pd/C (10 wt. %, 50 mg) in EtOH and AcOH (20 ml+1 ml) was reacted under hydrogen atmosphere at 50° C. for 2 hours. The catalyst was removed by filtration through a pad of Celite. After removal of the solvent in vacuo, the crude material was dissolved in EtOAc and washed with NaHCO3 solution and brine and dried over Na2SO4. The solvent was removed by rotary evaporation. The crude solid was purified by flash chromatography (EtOAc/hexane, 2:1) to give compound 20 (0.261 g, 72.4%). 1H NMR (300 MHz, CDCl3) δ 11.2 (1H, s), 7.22 (1H, s), 7.20 (1H, s), 7.16 (1H, brs), 7.10 (1H, s), 6.70-6.66 (1H, m), 3.69 (3H, s), 2.28 (2H, t, J=7.4 Hz), 2.06 (2H, dd, J=7.3, 4.7 Hz), 1.61-1.45 (4H, m), 1.22-1.08 (4H, m). 13C NMR (75 MHz, CDCl3) δ 174.6, 171.8, 159.6, 150.1, 147.3, 135.7, 130.2, 116.9, 115.3, 113.0, 108.1, 51.9, 36.1, 34.3, 29.07, 29.01, 25.09, 25.00, 21.4.

後処理

  1. customwas reacted under hydrogen atmosphere at 50° C. for 2 hours
  2. customThe catalyst was removed by filtration through a pad of Celite
  3. customAfter removal of the solvent in vacuo
  4. dissolutionthe crude material was dissolved in EtOAc
  5. washwashed with NaHCO3 solution and brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed by rotary evaporation
  8. customThe crude solid was purified by flash chromatography (EtOAc/hexane, 2:1)

出典と根拠

ORDレコード
ord-7d7cc4d73072448797ac305437d34c6e
出典データセット
uspto-grants-2014_02
特許番号
US08653278B2

関連ノート

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