Triphenylphosphine → (3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-N-(3-methoxyphenyl)-N-methyltetrahydrofuran-2-carboxamide

(3R,4R,5R)-3,4-Bis(benzoyloxy)-5-(benzoyloxymethyl)tetrahydrofuran-2-carboxylic acid (3,4,6-Tri-O-benzoyl-2,5-anhydro-D-allonic acid, 2 g, 4 mmol) was dissolved in anhydrous THF (40 mL) under argon. Triphenylphosphine (2.1 g, 8 mmol) was then added, and the resulting mixture was stirred until it was completely dissolved. Subsequently 2,2′-dipyridyldisulfide (1.8 g, 8 mmol) was added to the reaction mixture. The mixture was stirred at room temperature for 2 hours, after which 3-methoxy-N-methylaniline (0.7 g, 5.6 mmol) was added and stirring was continued at room temperature for 16 hours. The solvent was evaporated to dryness, the residue was dissolved in chloroform (150 mL), the solution was washed twice with 0.1M NaOH solution (100 mL), twice with 0.2 M HCl solution (100 mL), once with saturated NaHCO3 solution (100 mL), and dried (Na2SO4). The solution was evaporated to dryness and the residue dissolved in 7M solution of ammonia in methanol (250 mL). The solution was stirred for 16 hours at room temperature and evaporated to dryness. The residue was dissolved in chloroform and applied to a column of silica gel. Elution with a mixture of chloroform-methanol (3:1) and evaporation of the appropriate fractions yielded the title compound as a colorless oil (0.51 g, 1.7 mmol, 42%): MS (ES) m/z 399 [M+H+C6H15N]+, 296 [M−H]−.

1. dissolutionwas completely dissolved
2. stirringThe mixture was stirred at room temperature for 2 hours
3. stirringstirring
4. customThe solvent was evaporated to dryness
5. dissolutionthe residue was dissolved in chloroform (150 mL)
6. washthe solution was washed twice with 0.1M NaOH solution (100 mL), twice with 0.2 M HCl solution (100 mL), once with saturated NaHCO3 solution (100 mL)
7. dry with materialdried (Na2SO4)
8. customThe solution was evaporated to dryness
9. dissolutionthe residue dissolved in 7M solution of ammonia in methanol (250 mL)
10. stirringThe solution was stirred for 16 hours at room temperature
11. customevaporated to dryness
12. dissolutionThe residue was dissolved in chloroform
13. washElution
14. additionwith a mixture of chloroform-methanol (3:1) and evaporation of the appropriate fractions

ORD record

ord-15c7f121f32943a0a4f6c3d3a75e8afa

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569259B2