{2-(benzyloxy)-5-[(1R)-2-({2-[4-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}amino)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanol → 4-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)ethyl]-2-(hydroxymethyl)phenol

HRID 1433283Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433283
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:59][Si:60]([C:63]([CH3:66])([CH3:65])[CH3:64])([CH3:62])[CH3:61])[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35]CC4C=CC=CC=4)=[C:31]([C@@H:43]([C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[CH2:44][CH2:45][N:46]([CH:50]([CH3:52])[CH3:51])[CH:47]([CH3:49])[CH3:48])[CH:30]=3)=[CH:22][CH:21]=2)=[CH:11][C:10]=1[CH2:67][OH:68])C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[Si:60]([O:59][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([CH2:67][OH:68])[CH:11]=1)[CH2:16][NH:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([C@@H:43]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[CH2:44][CH2:45][N:46]([CH:50]([CH3:52])[CH3:51])[CH:47]([CH3:49])[CH3:48])[CH:30]=2)=[CH:24][CH:25]=1)([C:63]([CH3:66])([CH3:64])[CH3:65])([CH3:62])[CH3:61]

Komponenten

4

Edukt 1

HCID 57933171{2-(benzyloxy)-5-[(1R)-2-({2-[4-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}amino)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanol

Produkt 1

HCID 579332144-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)ethyl]-2-(hydroxymethyl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

{2-(benzyloxy)-5-[(1R)-2-({2-[4-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}amino)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanol (Preparation 48, 280 mg, 0.30 mmol) was dissolved in ethanol (6 ml) and palladium hydroxide (20% by weight on carbon, 14 mg, 0.02 mmol) was added. The reaction was the hydrogenated under 40 psi at room temperature for 18 hours, cooled to room temperature and the reaction filtered through Celite™ and the filtrate solvent removed in vacuo to furnish the title compound as a gum, 235 mg.

Aufarbeitung

  1. customat room temperature
  2. customfor 18 hours
  3. filtrationthe reaction filtered through Celite™
  4. customthe filtrate solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-68296f679fee4f38af83be7dca9e1c68
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612084B2

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