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Ammonium formate → 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}formamide

HRID 1433265
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1433265
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:54][Si:55]([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56])[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([C@@H:38]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[CH2:39][CH2:40][N:41]([CH:45]([CH3:47])[CH3:46])[CH:42]([CH3:44])[CH3:43])[CH:32]=3)=[CH:22][CH:21]=2)=[CH:11][C:10]=1[NH:62][CH:63]=[O:64])C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[Si:55]([O:54][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:62][CH:63]=[O:64])[CH:11]=1)[CH2:16][NH:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([C@@H:38]([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)[CH2:39][CH2:40][N:41]([CH:45]([CH3:47])[CH3:46])[CH:42]([CH3:44])[CH3:43])[CH:32]=2)=[CH:22][CH:21]=1)([C:58]([CH3:61])([CH3:59])[CH3:60])([CH3:57])[CH3:56]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 2723923Ammonium formate3×HCID 57933207N-{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}formamide

Produkt 1

HCID 57933165N-{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}formamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysator3×HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

N-{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}formamide (Preparation 29, 400 mg, 0.45 mmol), ammonium formate (570 mg, 9.0 mmol) and 20% palladium hydroxide on carbon (60 mg) were mixed in methanol (8 ml) and stirred at 70° C. for 1 hour under nitrogen. Further ammonium formate (500 mg, 7.9 mmol) and 20% palladium hydroxide on carbon (50 mg) were then added and heating continued at 70° C. for further 1 hour. Reaction mixture was then cooled and filtered, the filtrate was collected and the solvent removed in vacuo. The residue was dissolved in methanol (8 ml) and ammonium formate (500 mg, 7.9 mmol) and 20% palladium hydroxide on carbon (50 mg) were added and stirred at 70° C. for 1 hour under nitrogen. Reaction mixture was then cooled and filtered, the filtrate was collected and the solvent removed in vacuo. The residue was dissolved in ethyl actate (25 ml) and saturated aqueous sodium hydrogen carbonate (25 ml). Organics were separated and washed with brine (15 ml), dried (magnesium sulphate) and solvent was removed in vacuo to furnish the title compound as a yellow solid, 280 mg.

Aufarbeitung

  1. temperatureheating
  2. waitcontinued at 70° C. for further 1 hour
  3. customReaction mixture
  4. temperaturewas then cooled
  5. filtrationfiltered
  6. customthe filtrate was collected
  7. customthe solvent removed in vacuo
  8. dissolutionThe residue was dissolved in methanol (8 ml)
  9. stirringstirred at 70° C. for 1 hour under nitrogen
  10. customReaction mixture
  11. temperaturewas then cooled
  12. filtrationfiltered
  13. customthe filtrate was collected
  14. customthe solvent removed in vacuo
  15. dissolutionThe residue was dissolved in ethyl actate (25 ml)
  16. customOrganics were separated
  17. washwashed with brine (15 ml)
  18. dry with materialdried (magnesium sulphate) and solvent
  19. customwas removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bda5e1122a7849e9baefbc8086b6629b
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07612084B2

Notizen zur Reaktion

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