N,N-Diethylethanamine trihydrofluoride → Ammonia

HRID 1433303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433303
[Si]([O:8][C@H:9]([C:46]1[CH:47]=[CH:48][C:49]([OH:55])=[C:50]([NH:52][CH:53]=[O:54])[CH:51]=1)[CH2:10][NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C@@H:30]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:31][CH2:32][N:33]([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])[CH:24]=2)=[CH:16][CH:15]=1)(C(C)(C)C)(C)C.CCN(CC)CC.F.F.F>CO.O1CCCC1>[NH3:11].[CH:37]([N:33]([CH:34]([CH3:36])[CH3:35])[CH2:32][CH2:31][C@@H:30]([C:25]1[CH:24]=[C:23]([CH2:22][CH2:21][O:20][C:17]2[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]([C:46]3[CH:47]=[CH:48][C:49]([OH:55])=[C:50]([NH:52][CH:53]=[O:54])[CH:51]=3)[OH:8])=[CH:15][CH:16]=2)[CH:28]=[CH:27][C:26]=1[OH:29])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([CH3:38])[CH3:39]

Komponenten

6

Edukt 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 57933190N-{5-[(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-hydroxyphenyl}formamide

Produkt 2

HCID 222AmmoniaHCID 57933198N-{5-[(1R)-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)-1-hydroxyethyl]-2-hydroxyphenyl}formamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-{5-[(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-hydroxyphenyl}formamide (Preparation 46, 180 mg, 0.18 mmol) was dissolved in methanol (5 ml) and tetrahydrofuran (10 ml), and triethylaminetrihydrofluoride (0.18 ml, 1.1 mmol) added. The mixture was stirred overnight and then the solvent removed in vacuo. The residue was dissolved in methanol (10 ml) and 880 ammonia (1 ml) and the solvent removed under reduced pressure. This was repeated and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (98/2/0.2 to 80/20/2.0 by volume) to furnish the title compound as a gum, 69 mg.

Aufarbeitung

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was dissolved in methanol (10 ml)
  3. custom880 ammonia (1 ml) and the solvent removed under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-1cad7a13285f4e9fb93ff90082773a62
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612084B2

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