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Sodium Carbonate → HCID 69069158, Verbindung

HRID 491150
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 491150
[CH3:1]OB(O)O.C([O-])([O-])=O.[Na+].[Na+].[NH2:12][C:13]1[C:45]([Cl:46])=[CH:44][C:16]([CH2:17][C@@H:18]([CH2:23][C:24](=[O:43])[N:25]2[CH2:30][CH2:29][CH:28]([N:31]3[CH2:37][CH2:36][C:35]4[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=4[NH:33][C:32]3=[O:42])[CH2:27][CH2:26]2)[C:19]([O:21][CH3:22])=[O:20])=[CH:15][C:14]=1Br>O1CCOCC1.CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:12][C:13]1[C:14]([CH3:1])=[CH:15][C:16]([CH2:17][C@@H:18]([CH2:23][C:24](=[O:43])[N:25]2[CH2:30][CH2:29][CH:28]([N:31]3[CH2:37][CH2:36][C:35]4[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=4[NH:33][C:32]3=[O:42])[CH2:27][CH2:26]2)[C:19]([O:21][CH3:22])=[O:20])=[CH:44][C:45]=1[Cl:46]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 14178740MethylboratHCID 69064064HCID 69064064, Verbindung

Produkt 1

HCID 69069158HCID 69069158, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator
HCID 887MethanolLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere 0.99 g (16.0 mmol) methylboric acid, 15.5 mL 2 M Na2CO3 solution and 1.02 g (1.40 mmol) Pd(dppf)Cl2 were added to a solution of 8.40 g (14.5 mmol) methyl(S)-2-(4-amino-3-bromo-5-chloro-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butanoate in 50 mL 1,4-dioxane and 3 mL MeOH and the reaction mixture was refluxed overnight. The reaction solution was filtered while hot and the filtrate was combined with EtOAc. The organic phase was washed several times with semisaturated NaHCO3 solution and dried over Na2SO4. It was filtered through activated charcoal and evaporated down i.vac. The residue was taken up in a little DCM and purified by chromatography (silica gel, gradient DCM to DCM/MeOH/NH3 90:10:1). The fractions containing the product were combined, evaporated down i.vac., triturated with DIPE, suction filtered and dried.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed overnight
  2. filtrationThe reaction solution was filtered while hot and the filtrate
  3. washThe organic phase was washed several times with semisaturated NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. filtrationIt was filtered through activated charcoal
  6. customevaporated down i.vac
  7. custompurified by chromatography (silica gel, gradient DCM to DCM/MeOH/NH3 90:10:1)
  8. additionThe fractions containing the product
  9. customevaporated down i.vac
  10. custom, triturated with DIPE, suction
  11. filtrationfiltered
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b929a4a669bc4c119e4d88c0df1fddac
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07528129B2

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