Hydrogen Peroxide → 1-[3-Cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-3-(2-hydroxy-propyl)-urea

HRID 1860158ノート

反応式

HRID 1860158 の反応式
[CH2:1]([NH:4][C:5]([NH:7][C:8](=[O:24])[CH:9]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)[CH2:10][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:6])[CH:2]=[CH2:3].B.[O:26]1CCCC1.C(=O)(O)[O-].[Na+].OO>O1CCCC1.C(O)C>[CH:11]1([CH2:10][CH:9]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[C:8]([NH:7][C:5]([NH:4][CH2:1][CH:2]([OH:26])[CH3:3])=[O:6])=[O:24])[CH2:15][CH2:14][CH2:13][CH2:12]1

参加物

7

反応物 4

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 186266071-Allyl-3-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-urea

生成物 1

HCID 186266211-[3-Cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-3-(2-hydroxy-propyl)-urea収率 26%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of 1-allyl-3-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-urea (prepared in Example 12B-e, 132 mg, 0.36 mmol) in tetrahydrofuran (10 mL) cooled to 0° C. was treated with a 1M solution of borane-tetrahydrofuran (0.7 mL, 0.72 mmol). The reaction mixture was allowed to warm from 0° C. to 25° C. over 1 h. At this time, the solution was re-cooled to 0° C. and treated with ethanol (2 mL) followed by the slow addition of a mixture of a saturated aqueous sodium bicarbonate solution (6 mL) and 30% hydrogen peroxide (2 mL). The resulting mixture was allowed to slowly warm to 25° C. over 1 h. At this time, the reaction was re-cooled to 0° C. and was slowly quenched with a saturated aqueous sodium sulfite solution (20 mL). This mixture was extracted with ethyl acetate (3×20 mL). The organics were washed with a saturated aqueous sodium chloride solution (1×15 mL), dried over sodium sulfate, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexaneslethyl acetate) effected the separation of two spots, the first of the two product spots to elute off the column afforded 1-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-3-(2-hydroxy-propyl)-urea (36 mg, 26%) as a white solid: mp 116.7-119.9° C.; EI-HRMS m/e calcd for C18H24Cl2N2O3 (M+) 386.1164, found 386.1173.

後処理

  1. temperatureto warm from 0° C. to 25° C. over 1 h
  2. temperatureto slowly warm to 25° C. over 1 h
  3. temperatureAt this time, the reaction was re-cooled to 0° C.
  4. customwas slowly quenched with a saturated aqueous sodium sulfite solution (20 mL)
  5. extractionThis mixture was extracted with ethyl acetate (3×20 mL)
  6. washThe organics were washed with a saturated aqueous sodium chloride solution (1×15 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customthe separation of two spots
  10. washthe first of the two product spots to elute off the column

出典と根拠

ORDレコード
ord-402ee6aa772f4d418bdeb7a1811f0681
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…