Benzylamine → HCID 10871345, Verbindung

HRID 928873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928873
C([O:4][CH:5]1[O:22][C@H:21]([C:23]([O:25][CH3:26])=[O:24])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.C(N)C1C=CC=CC=1>CN(C=O)C>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:21]([C:23]([O:25][CH3:26])=[O:24])[O:22][CH:5]1[OH:4])(=[O:10])[CH3:9]

Komponenten

4

Edukt 2

HCID 7504BenzylamineHCID 11047049Methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate

Produkt 1

HCID 10871345HCID 10871345, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl 1,2,3,4-tetra-O-acetyl-D-glucopyranuronate F13-2 (1.2 g, 3.2 mmol) was dissolved in dry DMF (10 mL) under N2. To the solution, benzylamine (0.42 mL, 3.8 mmol) was added. The mixture was stirred at r.t. for 16 hours. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (Hexane:EtOAc=1:2, by volume) to afford a white solid F13c in 84% yield. 1H NMR (600 MHz, CDCl3) δ 5.50-5.55 (m, 1H), 5.11-5.27 (m, 1H), 4.85-4.91 (m, 1H), 5.39-4.56 (m, 2H), 3.70-3.72 (m, 3H), 1.99-2.05 (m, 9H). 13C NMR (150 MHz, CDCl3) δ 170.68, 170.45, 170.34, 170.30, 169.94, 169.81, 168.77, 167.83, 95.59, 90.36, 72.98, 72.66, 71.81, 70.97, 69.73, 69.61, 69.34, 68.12, 53.21, 53.11, 20.85, 20.84, 20.77, 20.70, 20.66, 20.65.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (Hexane:EtOAc=1:2, by volume)
  3. customto afford a white solid F13c in 84% yield

Quellen und Nachweise

ORD-Eintrag
ord-f3dc00089e5f4777b5757fc6d398f3d2
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290530B2

Notizen zur Reaktion

Wird geladen…