Citric Acid → 1-(beta-D-glucopyranosyl)-3-(5-(6-fluoro-3-pyridyl)-2-thienyl-methyl)-4-methylbenzene

HRID 1625729Notes

Reaction equation

HRID 1625729 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH2:31][C:32]2[S:33][C:34]([C:37]3[CH:38]=[N:39][C:40]([F:43])=[CH:41][CH:42]=3)=[CH:35][CH:36]=2)[CH:25]=1)(=O)C.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1.O1CCCC1>[C@@H:6]1([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH2:31][C:32]3[S:33][C:34]([C:37]4[CH:38]=[N:39][C:40]([F:43])=[CH:41][CH:42]=4)=[CH:35][CH:36]=3)[CH:25]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 666084961-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-3-(5(6-fluoro-3-pyridyl)-2-thienylmethyl)-4-methylbenzene

Product 1

HCID 529174341-(beta-D-glucopyranosyl)-3-(5-(6-fluoro-3-pyridyl)-2-thienyl-methyl)-4-methylbenzeneYield 120.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

The above 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-(5(6-fluoro-3-pyridyl)-2-thienylmethyl)-4-methylbenzene 59 (39 mg) was dissolved in 1,4-dioxane (4 ml)-tetrahydrofuran (4 ml), and added thereto was 2N sodium hydroxide (2 ml). The mixture was stirred at room temperature for one hour. The mixture was made acidic by addition of an aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with a saturated aqueous sodium hydrogen carbonate solution and brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure to give the desired 1-(β-D-glucopyranosyl)-3-(5-(6-fluoro-3-pyridyl)-2-thienylmethyl)-4-methylbenzene 60 (34 mg) as colorless powder. APCI-Mass m/Z 463 (M+NH4).

Workup

  1. additionadded
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with a saturated aqueous sodium hydrogen carbonate solution and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f6c99cacff794b729abb53dc4a611b9c
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

Loading…