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

HRID 1488261Notes

Reaction equation

HRID 1488261 reaction equation
[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]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 103663,5-Pyridinedicarboxylic acidHCID 109547442-Aminoethyl alpha-l-fucopyranoside

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-75a476381eff48d78dfb0ac4220e2aef
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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