Potassium Iodide → Ammonia

HRID 1433250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433250
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[CH:39]=[CH:38][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C@@H:22]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:23][CH2:24][N:25]([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH:16]=2)=[CH:8][CH:7]=1.[CH2:40]([O:47][C:48]1[CH:53]=[CH:52][C:51]([C@@H:54]([O:57][Si:58]([C:61]([CH3:64])([CH3:63])[CH3:62])([CH3:60])[CH3:59])[CH2:55]Br)=[CH:50][C:49]=1[NH:65][S:66]([CH3:69])(=[O:68])=[O:67])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(=O)([O-])O.[Na+].[I-].[K+]>O.C(#N)C>[NH3:3].[CH2:40]([O:47][C:48]1[CH:53]=[CH:52][C:51]([C@@H:54]([O:57][Si:58]([C:61]([CH3:62])([CH3:64])[CH3:63])([CH3:60])[CH3:59])[CH2:55][NH:3][CH2:4][CH2:5][C:6]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C@@H:22]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:23][CH2:24][N:25]([CH:26]([CH3:28])[CH3:27])[CH:29]([CH3:30])[CH3:31])[CH:16]=3)=[CH:38][CH:39]=2)=[CH:50][C:49]=1[NH:65][S:66]([CH3:69])(=[O:67])=[O:68])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Komponenten

8

Edukt 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 46938715N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-([tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamideHCID 866164804-{4-[4-(2-Aminoethyl)phenoxy]butyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol bis hydrochloride salt

Produkt 2

HCID 222AmmoniaHCID 57933232N-{2-(Benzyloxy)-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]phenyl}methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

4-{4-[4-(2-aminoethyl)phenoxy]butyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol bis hydrochloride salt (Preparation 13, 420 mg, 0.73 mmol), N-{2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanesulfonamide (Prepared according to WO2005/080324, 375 mg, 0.73 mmol), sodium hydrogen carbonate (245 mg, 2.92 mmol) and potassium iodide (121 mg, 0.73 mmol) were added to acetonitrile (15 ml) and heated to 90° C. for 30 minutes and left at room temperature for 48 hours, water was added and extracted with ethyl acetate, dried (magnesium sulphate) and the solvent removed in vacuo, the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (971310.3 to 92/810.8 by volume) to furnish the title compound as a white foam, 207 mg.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (magnesium sulphate)
  3. customthe solvent removed in vacuo
  4. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-cdee056ef52248b4bb45571a676bef36
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612084B2

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