3-{2-[(2R)-2-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(tert-butyldimethyl-silanyloxy)ethylamino]-2-methylpropyl}benzoic acid methyl ester → 3-(2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid methyl ester

HRID 1866511Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1866511
[CH3:1][O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]([NH:14][CH2:15][C@@H:16]([C:25]2[CH:30]=[CH:29][C:28]([O:31]CC3C=CC=CC=3)=[C:27]([CH2:39][OH:40])[CH:26]=2)[O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])([CH3:13])[CH3:12])[CH:5]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]([NH:14][CH2:15][C@H:16]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH2:39][OH:40])[CH:26]=2)([CH3:13])[CH3:12])[CH:5]=1

Komponenten

4

Edukt 1

HCID 579782283-{2-[(2R)-2-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(tert-butyldimethyl-silanyloxy)ethylamino]-2-methylpropyl}benzoic acid methyl ester

Produkt 1

HCID 690248003-(2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

3-{2-[(2R)-2-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(tert-butyldimethyl-silanyloxy)ethylamino]-2-methylpropyl}benzoic acid methyl ester (Preparation 35) (2.12 g, 3.70 mmol) and palladium-on-carbon (10%, 300 mg) in methanol (50 ml) were hydrogenated at room temperature and 60 psi for 18 hours. The reaction mixture was filtered through arbocel and the filtrate concentrated in vacuo, the residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5 by volume) to furnish the title compound, this material was taken up in diethylether and evaporated (×3) to yield a white foam (1.50 g).

Aufarbeitung

  1. customwere hydrogenated at room temperature
  2. filtrationThe reaction mixture was filtered through arbocel
  3. concentrationthe filtrate concentrated in vacuo
  4. customthe residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-10f24f8a6028464fa839fe5c6d49600b
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629358B2

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