Toluene → HCID 178420607, Verbindung

HRID 20924

Reaktionsgleichung

Reaktionsgleichung von HRID 20924
COC1C=CC(C(C2C=CC(OC)=CC=2)OC(C2C=CC=CC=2)[CH:12]2[CH:16](O)[CH2:15][N:14](C(=O)CCCCC[N:24]3[C:32](=[O:33])[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]3=[O:34])[CH2:13]2)=CC=1.C1(C)C=CC=CC=1.C(CC[O:61][P:62]([N:70](C(C)C)C(C)C)N(C(C)C)C(C)C)#N.C(OCC)(=[O:79])C>CCCCCC>[NH:14]1[CH2:15][CH2:16][CH2:12][CH2:13]1.[P:62]([NH2:70])([O-:61])[O:79][N:24]1[C:32](=[O:33])[C:31]2=[CH:30][CH:29]=[CH:28][CH:27]=[C:26]2[C:25]1=[O:34]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 1281532-Cyanoethyl tetraisopropylphosphorodiamiditeHCID 1317282252-(6-{3-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-isoindole-1,3-dione

Produkt 1

HCID 178420607HCID 178420607, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Compound 77 (1.5 g, 2.26 mmol) was coevaporated with anhydrous toluene (25 mL). To the residue N,N-tetraisopropylammonium tetrazolide (0.127 g, 1.13 mmol) was added and the mixture was dried over P2O5 in a vacuum oven for overnight at 40° C. The reaction mixture was dissolved in acetonitrile/dichloroethane (10 mL) and 2-cyanoethyl-N,N,N′,N′-tetraisopropylphosphorodiamidite (1.362 g, 1.49 mL, 4.52 mmol) was added. The reaction mixture was stirred at ambient temperature for overnight. The completion of the reaction was ascertained by TLC (Rf=0.4 in 1:1 ethyl acetate:hexane). The reaction mixture was concentrated undervacuum and the residue was dissolved in ethyl acetate (100 mL). The organic layer was washed with 5% NaHCO3 (100 mL) and brine (100 mL). The organic layer was dried over anhydrous Na2SO4 filtered and concentrated under reduced pressure. The residue was purified over silica gel (50:49:1, EtOAc:Hexane:triethlyamine) to afford compound 78 as white solid (1.66 g, 85%).

Aufarbeitung

  1. dry with materialthe mixture was dried over P2O5 in a vacuum oven for overnight at 40° C
  2. dissolutionThe reaction mixture was dissolved in acetonitrile/dichloroethane (10 mL)
  3. concentrationThe reaction mixture was concentrated undervacuum
  4. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  5. washThe organic layer was washed with 5% NaHCO3 (100 mL) and brine (100 mL)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified over silica gel (50:49:1, EtOAc:Hexane:triethlyamine)

Quellen und Nachweise

ORD-Eintrag
ord-9aed5765be684fe0a265b91036b54089
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745608B2

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