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

HRID 1860164노트

반응식

HRID 1860164 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:22]=[C:23]=[O:24])[CH:20]=[CH2:21]>C1(C)C=CC=CC=1>[CH2:19]([NH:22][C:23]([NH:10][C:8](=[O:9])[C@@H:7]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=1)[CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:24])[CH:20]=[CH2:21]

참가 물질

4

반응물 2

HCID 15123Allyl isocyanateHCID 462222313-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionamide

생성물 1

HCID 120444671-allyl-3-[3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl]-urea수율 81%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
25 °C

실험 절차

A solution of 3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionamide (prepared in Example 13, 1.02 g, 3.55 mmol) in toluene (30 mL) was treated with allyl isocyanate (0.47 mL, 5.33 mmol). This solution was heated to reflux for 16 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10 hexanes/ethyl acetate) afforded 1-allyl-3-[3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl]-urea (1.06 g, 81%) as a colorless oil: [α]23589=25.2° (c=0.151, chloroform); EI-HRMS m/e calcd for C18H22Cl2N2O2 (M+) 368.1058, found 368.1054.

후처리

  1. temperatureThis solution was heated
  2. temperatureto reflux for 16 h
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e0ca28096cd14e4f933289f02a19ccea
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06528543B1

반응 노트

불러오는 중…