Ammonia → Ammonia

HRID 1433296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433296
[Si]([O:8][C@H:9]([C:48]1[CH:49]=[CH:50][C:51]([OH:59])=[C:52]([NH:54][S:55]([CH3:58])(=[O:57])=[O:56])[CH:53]=1)[CH2:10][NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([C@@H:32]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:33][CH2:34][N:35]([CH:39]([CH3:41])[CH3:40])[CH:36]([CH3:38])[CH3:37])[CH:26]=2)=[CH:16][CH:15]=1)(C(C)(C)C)(C)C.F.F.F.C(N(CC)CC)C.N>O1CCCC1.[Cl-].[Na+].O>[NH3:11].[CH:39]([N:35]([CH:36]([CH3:38])[CH3:37])[CH2:34][CH2:33][C@@H:32]([C:27]1[CH:26]=[C:25]([CH2:24][CH2:23][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:48]3[CH:49]=[CH:50][C:51]([OH:59])=[C:52]([NH:54][S:55]([CH3:58])(=[O:57])=[O:56])[CH:53]=3)[OH:8])=[CH:15][CH:16]=2)[CH:30]=[CH:29][C:28]=1[OH:31])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)([CH3:41])[CH3:40]

Komponenten

7

Edukt 3

HCID 222AmmoniaHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 57933182N-{5-[(1R)-1-{[tert-Butyl(dimethyl)silyl]oxy}-2-({2-[4-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)ethyl]-2-hydroxyphenyl}methanesulfonamide

Produkt 2

HCID 222AmmoniaHCID 54583100N-(5-((R)-2-(4-(4-(3-((R)-3-(diisopropylamino)-1-phenylpropyl)-4-hydroxyphenyl)butoxy)phenethylamino)-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

N-{5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)ethyl]-2-hydroxyphenyl}methanesulfonamide (Preparation 15, 190 mg, 0.22 mmol) was dissolved in tetrahydrofuran (5 ml) and N,N-diethylethanamine trihydrofluoride (0.2 ml, 1 mmol) was added dropwise. After 29 hours a mixture of tetrahydrofuran (5 ml) and 880 ammonia (5 ml) were added and after 15 minutes brine was added, the organic layer was separated, dried (magnesium sulphate), filtered, the solvents were removed in vacuo and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (981210.2 to 92/8/0.8 by volume) to furnish the title compound as a white foam, 90 mg.

Aufarbeitung

  1. additionwas added
  2. customthe organic layer was separated
  3. dry with materialdried (magnesium sulphate)
  4. filtrationfiltered
  5. customthe solvents were removed in vacuo
  6. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-c736309ff94843ebb2cf1fedbab0a45f
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612084B2

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