ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Cyclohexylisopropylamine → 3-(2,4-Dichloro-pyrimidin-5-yl)-2-(3,5-dimethoxy-phenyl)-propionic acid methyl ester

HRID 11769
ノート
印刷プレビュー

反応式

HRID 11769 の反応式
C(NC1CCCCC1)(C)C.C([Li])CCC.[CH3:16][O:17][C:18](=[O:30])[CH2:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[CH:21]=1.[Cl:31][C:32]1[N:37]=[C:36]([Cl:38])[C:35]([CH2:39]I)=[CH:34][N:33]=1>O1CCCC1.C(OCC)(=O)C>[CH3:16][O:17][C:18](=[O:30])[CH:19]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[CH:21]=1)[CH2:39][C:35]1[C:36]([Cl:38])=[N:37][C:32]([Cl:31])=[N:33][CH:34]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 62386CyclohexylisopropylamineHCID 592191Methyl 3,5-dimethoxyphenylacetateHCID 219393522,4-Dichloro-5-(iodomethyl)pyrimidineHCID 178418339Butyllithium

生成物 1

HCID 210443203-(2,4-Dichloro-pyrimidin-5-yl)-2-(3,5-dimethoxy-phenyl)-propionic acid methyl ester

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
3 回
HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

To a solution of N-isopropylcyclohexylamine (1.44 g, 10.0 mmol) (Aldrich) in dry tetrahydrofuran (20 mL) was added n-butyllithium (2.5 M in hexanes, 4.0 mL, 10.0 mmol) (Aldrich) at −78° C. under argon. After 30 minutes, a solution of 3,5-dimethoxy-phenyl-acetic acid methyl ester (2.05 g, 9.76 mmol) (from Example 3a supra) in tetrahydrofuran (5 mL) was added by injection via a syringe and the reaction mixture was stirred at −78° C. for another 30 minutes. To this reaction mixture was added a solution of 2,4-dichloro-5-iodomethyl-pyrimidine (1.45 g, 5.0 mmol) (from Example 1c supra) in tetrahydrofuran (5 mL) at −78° C. and the reaction mixture was stirred at the same temperature for 1 hour then slowly allowed to warm up to −30° C. and stirred for 10 minutes. The reaction mixture was diluted with ethyl acetate (100 mL) and successively washed with saturated aqueous ammonium chloride solution (100 mL), water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography to give 3-(2,4-dichloro-pyrimidin-5-yl)-2-(3,5-dimethoxy-phenyl)-propionic acid methyl ester as a colorless oil. (Yield 1.45 g, 78.0%).

後処理

  1. stirringthe reaction mixture was stirred at the same temperature for 1 hour
  2. temperatureto warm up to −30° C.
  3. stirringstirred for 10 minutes
  4. washsuccessively washed with saturated aqueous ammonium chloride solution (100 mL), water (50 mL) and brine (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-ccebbc825e74486f8f8653f180c27aab
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07098332B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート