3-Nitrobenzoic acid → Biphenyl indolizinyl nitrobenzoate

HRID 1488661

Reaktionsgleichung

Reaktionsgleichung von HRID 1488661
N([C:8]([O:10]CC)=[O:9])=NC(OCC)=O.[N+:13](C1C=C(C=CC=1)C(O)=O)([O-:15])=[O:14].O[C:26]1N=N[NH:29][CH:30]=1.[C:31]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CCOCC.C(OCC)(=O)C>[C:31]1([C:37]2[C:38]([N+:13]([O-:15])=[O:14])=[C:39]([CH:40]=[CH:41][CH:42]=2)[C:8]([OH:10])=[O:9])[CH:26]=[CH:30][N:29]2[C:36]=1[CH:35]=[CH:34][CH:33]=[CH:32]2.[C:31]1([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

8

Edukt 4

HCID 84973-Nitrobenzoic acidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178516797HCID 178516797, Verbindung

Produkt 1

HCID 86748744Biphenyl indolizinyl nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Alternatively, the biphenyl trans-hydroxy triazole can be prepared using the Mitsunobu reaction conditions. To a solution of diethyl azodicarboxylate (2.0 mmol) and 3-nitrobenzoic acid (2.0 mmol) in 2.0 mL of THF is added dropwise a solution of the biphenyl hydroxy triazole (2.0 mmol, obtained from Step 1 of Example 3261), and triphenylphosphine (2.0 mmol) in 1.0 mL of THF at room temperature. The resulting solution is stirred at room temperature until the reaction is complete. The resulting mixture is diluted with ether or ethyl acetate, and washed with water. The extracts are dried (MgSO4) and concentrated in vacuo to give the biphenyl indolizinyl nitrobenzoate. The crude benzoate is hydrolyzed with LiOH in aqueous THF at room temperture and purified to give the biphenyl trans-hydroxy triazole.

Aufarbeitung

  1. customthe Mitsunobu reaction conditions
  2. washwashed with water
  3. dry with materialThe extracts are dried (MgSO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cdc9140e847047f980fa018cf359010f
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05674879

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