Ethyl isocyanate → 1-[3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl]-3-ethyl-urea

HRID 1860152ノート

反応式

HRID 1860152 の反応式
[CH:1]1([CH2:6][C@H:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([NH2:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:19]([N:21]=[C:22]=[O:23])[CH3:20]>C1(C)C=CC=CC=1>[CH:1]1([CH2:6][C@H:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([NH:10][C:22]([NH:21][CH2:19][CH3:20])=[O:23])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 8022Ethyl isocyanateHCID 462222313-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionamide

生成物 1

HCID 120444611-[3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl]-3-ethyl-urea収率 42%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionamide (prepared in Example 13, 103 mg, 0.36 mmol) in toluene (10 mL) was treated with ethyl isocyanate (40 μL, 0.54 mmol). The resulting reaction mixture was heated under reflux for 24 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 4/1 hexanes/ethyl acetate) afforded 1-[3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl]-3-ethyl-urea (54 mg, 42%) as a white foam: [α]23589=−41.9° (c=0.031, chloroform); FAB-HRMS m/e calcd for C17H22Cl2N2O2 (M+H)+357.1136, found 357.1137.

後処理

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 24 h
  4. concentrationThe reaction mixture was then concentrated in vacuo

出典と根拠

ORDレコード
ord-9657553a580045e786b09318bbf27cf0
出典データセット
uspto-grants-2003_03
特許番号
US06528543B1

反応ノート

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