N,N-Diethylethanamine trihydrofluoride → Ammonia

HRID 1433299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433299
[Si]([O:8][C@H:9]([C:46]1[CH:47]=[CH:48][C:49]([OH:57])=[C:50]([NH:52][S:53]([CH3:56])(=[O:55])=[O:54])[CH:51]=1)[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C@@H:30]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:31][CH2:32][N:33]([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])[CH:24]=1)(C(C)(C)C)(C)C.CCN(CC)CC.F.F.F>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][CH2:20][CH2:19][O:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]([C:46]2[CH:47]=[CH:48][C:49]([OH:57])=[C:50]([NH:52][S:53]([CH3:56])(=[O:55])=[O:54])[CH:51]=2)[OH:8])[CH:28]=[CH:27][C:26]=1[OH:29])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([CH3:39])[CH3:38]

Komponenten

5

Edukt 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 57933211N-{5-[(1R)-1-{[tert-Butyl(dimethyl)silyl]oxy}-2-{[6-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexyl]amino}ethyl]-2-hydroxyphenyl}methanesulfonamide

Produkt 2

HCID 222AmmoniaHCID 54582151N-(5-((R)-2-(6-(4-(3-((R)-3-(diisopropylamino)-1-phenylpropyl)-4-hydroxyphenyl)butoxy)hexylamino)-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-{5-[(1R)-1-{[tert-Butyl(dimethyl)silyl]oxy}-2-{[6-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexyl]amino}ethyl]-2-hydroxyphenyl}methanesulfonamide (Preparation 28, 420 mg, 0.51 mmol) was dissolved in tetrahydrofuran (6 ml) and triethylaminetrihydrofluoride (415 ul, 2.55 mmol) was added. The reaction was stirred at room temperature for 4 hours and the solvent removed in vacuo, the residue was dissolved in methanol (1 ml) and 880 ammonia (1 ml) and the solvent removed in vacuo, the residue was dissolved in methanol (1 ml) and 880 ammonia (1 ml) and the solvent removed in vacuo. The resulting oil was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (89/11/1.1 by volume) to furnish the title compound as a yellow solid, 26 mg.

Aufarbeitung

  1. customthe solvent removed in vacuo
  2. dissolutionthe residue was dissolved in methanol (1 ml)
  3. custom880 ammonia (1 ml) and the solvent removed in vacuo
  4. dissolutionthe residue was dissolved in methanol (1 ml)
  5. custom880 ammonia (1 ml) and the solvent removed in vacuo
  6. customThe resulting oil was purified by column chromatography on silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-3b51118523724995ac2c42c9de886b94
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612084B2

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