1,2-Dichloroethane → N,N'-bis{2-[(alpha-L-fucopyranosyl)oxy]ethyl}pyridine-3,5-dicarboxamide

HRID 1488261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488261
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=O)[CH:4]=[C:3]([C:10]([OH:12])=O)[CH:2]=1.[O:13]([CH2:24][CH2:25][NH2:26])[C@@H:14]1[O:22][C@@H:21]([CH3:23])[C@@H:19]([OH:20])[C@@H:17]([OH:18])[C@@H:15]1[OH:16].[CH2:27](Cl)[CH2:28]Cl>CN(C=O)C.CN(C1C=CN=CC=1)C>[C@@H:14]1([O:13][CH2:24][CH2:25][NH:26][C:7]([C:5]2[CH:6]=[N:1][CH:2]=[C:3]([C:10]([NH:26][CH2:25][CH2:24][O:13][C@@H:14]3[O:22][C@@H:27]([CH3:28])[C@@H:19]([OH:20])[C@@H:17]([OH:18])[C@@H:15]3[OH:16])=[O:12])[CH:4]=2)=[O:9])[O:22][C@@H:21]([CH3:23])[C@@H:19]([OH:20])[C@@H:17]([OH:18])[C@@H:15]1[OH:16]

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 103663,5-Pyridinedicarboxylic acidHCID 10954744(2R,3S,4R,5S,6S)-2-(2-Aminoethoxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

Produkt 1

HCID 117995843N,N'-bis{2-[(alpha-L-fucopyranosyl)oxy]ethyl}pyridine-3,5-dicarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 3,5-pyridinedicarboxylic acid (311 mg, 1.861 mmol) in DMF (30 mL) at room temperature was added 2-aminoethyl α-L-fucopyranoside (2.077 g, 9.30 mmol), DMAP (568 mg, 4.65 mmol), and EDC (1784 mg, 9.30 mmol). After stirring at room temperature for 16 hours, the reaction mixture was concentrated. The residue was purified by flash chromatography on C18 reverse phase silica gel (300 g), eluting with AcCN in water) to give the title compound. UPLC Method B: m/e=578.31 [M+1]; Rt=0.25 min.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was purified by flash chromatography on C18 reverse phase silica gel (300 g)
  3. washeluting with AcCN in water)

Quellen und Nachweise

ORD-Eintrag
ord-75a476381eff48d78dfb0ac4220e2aef
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09427475B2

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