Triphenylphosphine → 3-(2-Tert-butoxycarbonylamino-3-cyanopropoxy)-5-chloro-1,2-benzoisoxazole

HRID 1901646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1901646
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][OH:14])[CH2:10][C:11]#[N:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[O:23][N:22]=[C:21](O)[C:20]=2[CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:10][C:11]#[N:12])[CH2:13][O:14][C:21]1[C:20]2[CH:25]=[C:16]([Cl:15])[CH:17]=[CH:18][C:19]=2[O:23][N:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 233684013-Tert-butoxycarbonylamino-4-hydroxybutyronitrileHCID 178518984HCID 178518984, Verbindung

Produkt 1

HCID 233685283-(2-Tert-butoxycarbonylamino-3-cyanopropoxy)-5-chloro-1,2-benzoisoxazoleAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1.0 g of 3-tert-butoxycarbonylamino-4-hydroxybutyronitrile in 15 ml of tetrahydrofuran are added 0.85 g of 5-chloro-3-hydroxy-1,2-benzoisoxazole, 1.71 g of triphenylphosphine and 1.14 g of diethyl azodicarboxylate with ice-cooling, and they are subjected to reaction at room temperature for 24 hours. Thereafter, the solvent is removed by distillation under reduced pressure. The residue obtained is purified by a column chromatography [eluant:n-hexane:ethyl acetate=5:1], to obtain 1.29 g of 3-(2-tert-butoxycarbonylamino-3-cyanopropoxy)-5-chloro-1,2-benzoisoxazole having a melting point of 147.2°-147.9° C.

Aufarbeitung

  1. temperaturecooling
  2. customthey are subjected to reaction at room temperature for 24 hours
  3. customThereafter, the solvent is removed by distillation under reduced pressure
  4. customThe residue obtained
  5. customis purified by a column chromatography [eluant:n-hexane:ethyl acetate=5:1]

Quellen und Nachweise

ORD-Eintrag
ord-b39617b293f647c59877bef2b54d72db
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05578627

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