Methyl Isocyanate → 1-[3-Cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl]-3-methyl-urea

HRID 1860145노트

반응식

HRID 1860145 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.[CH3:19][N:20]=[C:21]=[O:22]>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:21]([NH:20][CH3:19])=[O:22])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 12228Methyl IsocyanateHCID 462222313-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionamide

생성물 1

HCID 120444601-[3-Cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl]-3-methyl-urea수율 63%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionamide (54 mg, 0,19 mmol) in toluene (5 mL) was treated with methyl isocyanate (0.03 mL, 0.47 mmol). The resulting solution was heated under reflux for 24 h. At this time, the reaction was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh 70/30 hexanes/ethyl acetate) afforded 1-[3-cyclopentyl-2(R)-(3,4-dichloro-phenyl)-propionyl]-3-methyl-urea (40 mg, 63%) as a white solid: mp 124.8-127.5° C.; [α]23589=−21.2° (c=0.099, chloroform); EI-HRMS m/e calcd for C16H20Cl2N2O2 (M+) 342.0902, found 342.0902.

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 24 h
  3. concentrationAt this time, the reaction was concentrated in vacuo

출처 및 근거

ORD 기록
ord-7746632ba5ea4657beeca392eabdca2f
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06528543B1

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