Hydrogen Peroxide → (2-{3-Chloro-5-[cyclopentyl-(3-hydroxy-propyl)-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester

HRID 2268577Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2268577
[C:1]([O:5][C:6](=[O:35])[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([C:24](=[O:34])[N:25]([CH2:31][CH:32]=[CH2:33])[CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:18]=1)[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].B1C2CCCC1CCC2.[OH:45]O.[OH-].[Na+]>>[C:1]([O:5][C:6](=[O:35])[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([C:24](=[O:34])[N:25]([CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)[CH2:31][CH2:32][CH2:33][OH:45])[CH:20]=[C:21]([Cl:23])[CH:22]=1)[C:8]1[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=1)([CH3:3])([CH3:2])[CH3:4]

Komponenten

5

Edukt 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 18349220{2-[3-(Allyl-cyclopentyl-carbamoyl)-5-chloro-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester

Produkt 1

HCID 54299674(2-{3-Chloro-5-[cyclopentyl-(3-hydroxy-propyl)-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester

Versuchsvorschrift

To {2-[3-(allyl-cyclopentyl-carbamoyl)-5-chloro-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester (0.11 g) was added 9-BBN (0.5M in THF, 2.2 ml) and the resulting solution stirred at room temperature under nitrogen for 20 h. A mixture of 28% aqueous hydrogen peroxide solution (1.8 ml) and 2M aqueous sodium hydroxide (0.9 ml) was added and the reaction mixture stirred at reflux for 2 h. The solvent was removed in vacuo and the residue purified by preparative hplc and the title compound (0.064 g) was obtained as a colourless gum by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction mixture stirred
  3. temperatureat reflux for 2 h
  4. customThe solvent was removed in vacuo
  5. customthe residue purified by preparative hplc

Quellen und Nachweise

ORD-Eintrag
ord-48b3b67fe6e94ece89c844e6001e708d
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326386B1

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