Trichloroacetonitrile → 2,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate

HRID 864697Notes

Reaction equation

HRID 864697 reaction equation
[H-].[Na+].[C:3]([O:6][C@@H:7]1[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:12]([O:18][C:19](=[O:21])[CH3:20])[C@@H:11]([C:22]([O:24][CH3:25])=[O:23])[O:10][CH:8]1[OH:9])(=[O:5])[CH3:4].[Cl:26][C:27]([Cl:31])([Cl:30])[C:28]#[N:29]>ClCCl>[Cl:26][C:27]([Cl:31])([Cl:30])[C:28]([O:9][C@H:8]1[O:10][C@H:11]([C:22]([O:24][CH3:25])=[O:23])[C@@H:12]([O:18][C:19](=[O:21])[CH3:20])[C@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:7]1[O:6][C:3](=[O:5])[CH3:4])=[NH:29]

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 24758Sodium hydrideHCID 10871345HCID 10871345, compound

Product 1

HCID 109618152,3,4-Tri-O-acetyl-α-D-glucuronide methyl ester trichloroacetimidate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

60% Oily sodium hydride (0.366 g) was added to an ice-cooled solution of methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (3.96 g), trichloroacetonitrile (12 ml) and dichloromethane (100 ml), and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was subjected to short column (70 φ×50 mm) chromatography on silica gel and eluted with ethyl acetate/hexane (1:1). The eluate was concentrated under reduced pressure to obtain the desired compound (4.37 g) as crystals (mp: 108° C.).

Workup

  1. washeluted with ethyl acetate/hexane (1:1)
  2. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e42ed0ab849b4f338508e6bb5a1a63a9
Source dataset
uspto-grants-1996_10
Patent number
US05563129

Reaction notes

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