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

HRID 1860145ノート

反応式

HRID 1860145 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.[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

参加物

4

反応物 2

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

生成物 1

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

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 (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.

後処理

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

出典と根拠

ORDレコード
ord-7746632ba5ea4657beeca392eabdca2f
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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