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

HRID 1860159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1860159
[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][CH2:2][CH2:3][OH:26])=[O:6])=[O:24])[CH2:15][CH2:14][CH2:13][CH2:12]1

Komponenten

7

Edukt 4

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

Produkt 1

HCID 120444631-[3-Cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-3-(3-hydroxy-propyl)-ureaAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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 slowly warm from 0° C. to 25° C. over 1 h. At this time, the solution was re-cooled to 0° C. and ethanol (2 mL) followed by a mixture of a saturated aqueous sodium bicarbonate solution (6 mL) and 30% hydrogen peroxide (2 mL) was added slowly. This mixture was allowed to slowly warm to 25° C. while stirring for 1 h. At this time, the reaction was re-cooled to 0° C. and slowly quenched with a saturated aqueous sodium sulfite solution (20 mL). This solution 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 hexanes/ethyl acetate) effected the separation of two spots, the second of the two product spots to elute off the column afforded 1-[3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionyl]-3-(3-hydroxy-propyl)-urea (73 mg, 53%) as a white hygroscopic solid: EI-HRMS m/e calcd for C18H24Cl2N2O3 (M+) 386.1164, found 386.1172.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c91c4b52b133420485a8edf76dc8e232
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06528543B1

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