NBD-Cl → 2-Nbdlg

HRID 876094

Reaktionsgleichung

Reaktionsgleichung von HRID 876094
Cl[C:2]1[C:10]2[C:6](=[N:7][O:8][N:9]=2)[C:5]([N+:11]([O-:13])=[O:12])=[CH:4][CH:3]=1.Cl.[OH:15][CH:16]1[O:24][C@@H:23]([CH2:25][OH:26])[C@H:21]([OH:22])[C@@H:19]([OH:20])[C@@H:17]1[NH2:18]>CO.C([O-])(O)=O.[Na+]>[CH:3]1[CH:4]=[C:5]([N+:11]([O-:13])=[O:12])[C:6]2[C:10](=[N:9][O:8][N:7]=2)[C:2]=1[NH:18][C@@H:17]([C@H:19]([OH:20])[C@@H:21]([OH:22])[C@@H:23]([OH:24])[CH2:25][OH:26])[CH:16]=[O:15]

Komponenten

5

Edukt 2

HCID 25043NBD-ClHCID 45933886(3S,4S,5R,6S)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol;hydrochloride

Produkt 1

HCID 873081042-Nbdlg

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

In a brown flask, 4-chloro-7-nitro-2,1,3-benzoxadiazole (NBD-Cl) (483 mg) was placed and dissolved in methanol (14.0 ml). Under an argon atmosphere, a solution in which L-glucosamine hydrochloride (283 mg) was dissolved in 0.3 M NaHCO3 solution (5.57 ml) was added thereto, and the resulting mixture was stirred at room temperature. After 24 hours, methanol was removed by concentration under reduced pressure, and the resulting precipitates (unnecessary substances derived from NBD-Cl) were removed by filtration. The precipitates were washed with water, and the filtrate and the washing solution were combined, followed by purification by HPLC. A target fraction was collected and lyophilized, whereby a target product was obtained (yield: 102 mg, yield ratio: 23%).

Aufarbeitung

  1. additionwas added
  2. custommethanol was removed by concentration under reduced pressure
  3. customthe resulting precipitates (unnecessary substances derived from NBD-Cl)
  4. customwere removed by filtration
  5. washThe precipitates were washed with water
  6. customfollowed by purification by HPLC
  7. customA target fraction was collected
  8. customwhereby a target product was obtained
  9. custom(yield: 102 mg, yield ratio: 23%)

Quellen und Nachweise

ORD-Eintrag
ord-770289f1225e41208a4fa887337bc626
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08986656B2

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