Triphenylphosphine → 6-Methoxy-3-((pivaloyloxy)methyl)-7-(2-(1,2,3-triazol-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one

HRID 855724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 855724
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]1([CH2:25][CH2:26][OH:27])[CH:24]=[CH:23][N:22]=[N:21]1.O[C:29]1[CH:38]=[C:37]2[C:32]([C:33](=[O:47])[N:34]([CH2:39][O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[CH:35]=[N:36]2)=[CH:31][C:30]=1[O:48][CH3:49].N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[CH3:49][O:48][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][C:29]=1[O:27][CH2:26][CH2:25][N:20]1[CH:24]=[CH:23][N:22]=[N:21]1)[N:36]=[CH:35][N:34]([CH2:39][O:40][C:41](=[O:46])[C:42]([CH3:43])([CH3:44])[CH3:45])[C:33]2=[O:47]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 99892372-(1H-1,2,3-triazol-1-yl)ethan-1-olHCID 10804576(7-Hydroxy-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate

Produkt 1

HCID 105971686-Methoxy-3-((pivaloyloxy)methyl)-7-(2-(1,2,3-triazol-1-yl)ethoxy)-3,4-dihydroquinazolin-4-oneAusbeute 276,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triphenylphosphine (2.82 g, 10.7 mmol) was added to a solution of 2-(1,2,3-triazol-1-yl)ethanol (609 mg, 5.4 mmol), (J. Antib. 1993, 46, 177), and 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (1.1 g, 3.6 mmol), (prepared as described for the starting material in Example 7), in methylene chloride (70 ml), diethyl azodicarboxylate (600 μl, 10.7 mmol) was then added. After stirring for 2 hours at ambient temperature, the volatiles were removed by evaporation and the residue was purified by column chromatography eluting with methylene chloride/methanol (98/2) to give 6-methoxy-3-((pivaloyloxy)methyl)-7-(2-(1,2,3-triazol-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one (4 g, 97%).

Aufarbeitung

  1. custom(prepared
  2. customthe volatiles were removed by evaporation
  3. customthe residue was purified by column chromatography
  4. washeluting with methylene chloride/methanol (98/2)

Quellen und Nachweise

ORD-Eintrag
ord-2e50cdcb55c7431aac687eab2f62cba5
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262201B1

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