Ammonium formate → Ammonia

HRID 1433263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433263
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:52][Si:53]([C:56]([CH3:59])([CH3:58])[CH3:57])([CH3:55])[CH3:54])[CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([C@@H:36]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH2:37][CH2:38][N:39]([CH:43]([CH3:45])[CH3:44])[CH:40]([CH3:42])[CH3:41])[CH:30]=2)=[CH:11][C:10]=1[NH:60][S:61]([CH3:64])(=[O:63])=[O:62])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[NH3:17].[Si:53]([O:52][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:60][S:61]([CH3:64])(=[O:62])=[O:63])[CH:11]=1)[CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([C@@H:36]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH2:37][CH2:38][N:39]([CH:40]([CH3:42])[CH3:41])[CH:43]([CH3:45])[CH3:44])[CH:30]=1)([C:56]([CH3:59])([CH3:57])[CH3:58])([CH3:55])[CH3:54]

Komponenten

6

Edukt 2

HCID 2723923Ammonium formate2×HCID 57933222N-{2-(Benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-{[6-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexyl]amino}ethyl]phenyl}methanesulfonamide

Produkt 2

HCID 222AmmoniaHCID 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysator3×HCID 702EthanolLösungsmittel

Versuchsvorschrift

N-{2-(Benzyloxy)-5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-{[6-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexyl]amino}ethyl]phenyl}methanesulfonamide (Preparation 27, 530 mg, 0.55 mmol) was dissolved in ethanol and ammonium formate (700 mg, 10.9 mmol) and 10% palladium hydroxide on carbon (100 mg) was added. The reaction was heated under reflux for 12 hours, cooled to room temperature and further ammonium formate (600 mg, 9.37 mmol) and 10% palladium hydroxide on carbon (60 mg) added. The reaction was heated under reflux for 3 hours, cooled to room temperature and further 10% palladium hydroxide on carbon (60 mg) added. The reaction was heated under reflux for 3 hours, cooled to room temperature and filtered through Arbocel™. The filtrate solvent was removed in vacuo and the oil was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (80/20/2.0 by volume) to furnish the title compound as a yellow oil, 420 mg.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 12 hours
  3. temperatureThe reaction was heated
  4. temperatureunder reflux for 3 hours
  5. temperaturecooled to room temperature
  6. temperatureThe reaction was heated
  7. temperatureunder reflux for 3 hours
  8. temperaturecooled to room temperature
  9. filtrationfiltered through Arbocel™
  10. customThe filtrate solvent was removed in vacuo
  11. customthe oil was purified by column chromatography on silica gel eluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-9f1840b28bfa48cf94ebc3a37810c24e
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612084B2

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