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

HRID 1860152노트

반응식

HRID 1860152 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-9657553a580045e786b09318bbf27cf0
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06528543B1

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