Cyanuric chloride → N,N',N"-(1,3,5-triazine-2,4,6-triyl)-tris-(1-amino-1-desoxy-D-glucitol)

HRID 355470

Reaction equation

HRID 355470 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[NH2:10][CH2:11][C@@H:12]([C@H:14]([C@@H:16]([C@@H:18]([CH2:20][OH:21])[OH:19])[OH:17])[OH:15])[OH:13].[C:22](=[O:25])([O-])[O-].[K+].[K+]>O>[N:1]1[C:8]([NH:10][CH2:11][C@@H:12]([C@H:14]([C@@H:16]([C@@H:18]([CH2:20][OH:21])[OH:19])[OH:17])[OH:15])[OH:13])=[N:7][C:5]([NH:10][CH2:11][C@@H:12]([C@H:14]([C@@H:16]([C@@H:18]([CH2:20][OH:21])[OH:19])[OH:17])[OH:15])[OH:13])=[N:4][C:2]=1[NH:10][CH2:11][C@@H:12]([C@H:14]([C@@H:16]([C@@H:18]([CH2:22][OH:25])[OH:19])[OH:17])[OH:15])[OH:13]

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 11430Potassium CarbonateHCID 452501Glucamine

Product 1

HCID 54282659N,N',N"-(1,3,5-triazine-2,4,6-triyl)-tris-(1-amino-1-desoxy-D-glucitol)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

184 mg of cyanuric chloride, 543.5 mg of D-glucamine and 450 mg of potassium carbonate were stirred at room temperature in 10 ml of water for three days. The thus-obtained crude product was thereupon chromatographed on LiChroprep RP-18 silica gel with water and subsequently with water containing an increasing amount of methanol. The relevant fractions were lyophilized; N,N',N"-(1,3,5-triazine-2,4,6-triyl)-tris-(1-amino-1-desoxy-D-glucitol) was thus obtained as a colorless powder, MS: m/z 619.2 ([M+H]+).

Workup

  1. customThe thus-obtained crude product
  2. customwas thereupon chromatographed on LiChroprep RP-18 silica gel with water and subsequently with water containing an increasing amount of methanol

Sources & evidence

ORD record
ord-f347c46c7f684548ab38c55713a55352
Source dataset
uspto-grants-1998_11
Patent number
US05830920

Linked notes

Loading…