Boron trifluoride etherate → 1-O-trichloroethyl-2,3,4-tri-O-acetyl-alpha-D-glucopyranuronic acid methyl ester

HRID 40439

Reaction equation

HRID 40439 reaction equation
B(F)(F)F.CCOCC.[CH3:10][O:11][C:12](=[O:35])[C@H:13]1[O:22][C@@H:17](OC(=O)C)[C@H:16]([O:23][C:24](=[O:26])[CH3:25])[C@@H:15]([O:27][C:28](=[O:30])[CH3:29])[C@@H:14]1[O:31][C:32](=[O:34])[CH3:33].[Cl:36][C:37]([Cl:41])([Cl:40])[CH2:38][OH:39]>ClCCl>[CH3:10][O:11][C:12](=[O:35])[C@H:13]1[O:22][C@H:17]([O:39][CH2:38][C:37]([Cl:41])([Cl:40])[Cl:36])[C@H:16]([O:23][C:24](=[O:26])[CH3:25])[C@@H:15]([O:27][C:28](=[O:30])[CH3:29])[C@@H:14]1[O:31][C:32](=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8259TrichloroethanolHCID 95087Methyl 1,2,3,4-tetra-O-acetyl-beta-D-glucopyranuronate

Product 1

HCID 666170921-O-trichloroethyl-2,3,4-tri-O-acetyl-alpha-D-glucopyranuronic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BF3-Et2O (15 ml) was added dropwise to a cooled solution at 0° C. of 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid methyl ester (11.23 g, 0.03 mol) and 2,2,2-trichloroethanol (20 ml) in anhydrous dichloromethane (250 ml) under inert atmosphere. The mixture was stirred at room temperature overnight and then washed with 1N HCl (100 ml), water (100 ml) and brine (100 ml). The organic phase was dried over sodium sulphate, filtered and concentrated to dryness. 1-O-trichloroethyl-2,3,4-tri-O-acetyl-α-D-glucopyranuronic acid methyl ester 1 (8.95 g) was obtained after recrystallization of the crude product from ether.

Workup

  1. washwashed with 1N HCl (100 ml), water (100 ml) and brine (100 ml)
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d72437301d8f450c8e58c63d57e0df84
Source dataset
uspto-grants-2013_09
Patent number
US08530177B2

Linked notes

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