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

HRID 1860164ノート

反応式

HRID 1860164 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: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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-e0ca28096cd14e4f933289f02a19ccea
出典データセット
uspto-grants-2003_03
特許番号
US06528543B1

反応ノート

読み込み中…