p-Toluenesulfonic acid → {2-Chloro-4-[(2-{[2-(2-hydroxyethoxy)ethoxy]methyl}phenyl)amino]phenyl}(2-methylphenyl)methanone

HRID 1797303ノート

反応式

HRID 1797303 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22]C2CCCCO2)[CH:5]=[CH:4][C:3]=1[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37])=[O:30].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22])[CH:5]=[CH:4][C:3]=1[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37])=[O:30]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 10118970(2-Chloro-4-{[2-({2-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]ethoxy}methyl)phenyl]amino}phenyl)(2-methylphenyl)methanone

生成物 1

HCID 10203602{2-Chloro-4-[(2-{[2-(2-hydroxyethoxy)ethoxy]methyl}phenyl)amino]phenyl}(2-methylphenyl)methanone

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Compound 149 (5.68 g, 10.8 mmol) was dissolved in MeOH (100 mL) and p-toluenesulfonic acid (3.09 g, 16.3 mmol) was added. The solution was stirred at room temperature for 2 h. Aqueous NaHCO3 (5%, 100 mL) was added and the water phase was extracted with EtOAc (3×50 mL). The combined organic phases were washed with brine (50 mL), dried (MgSO4) and evaporated in vacuo. The crude product was purified by flash chromatography using EtOAc/Petroleum ether 1:1–3:2 as the eluent to afford the title compound as an orange oil.

後処理

  1. extractionthe water phase was extracted with EtOAc (3×50 mL)
  2. washThe combined organic phases were washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-7a5b4afd97664151bbbb237180954c8c
出典データセット
uspto-grants-2006_04
特許番号
US07034015B2

反応ノート

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