NBD-Cl → 2-Nbdlg

HRID 876094

Reaction equation

HRID 876094 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

HCID 873081042-Nbdlg

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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%).

Workup

  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%)

Sources & evidence

ORD record
ord-770289f1225e41208a4fa887337bc626
Source dataset
uspto-grants-2015_03
Patent number
US08986656B2

Linked notes

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