Reacción #57476

Ecuación de reacción

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-2-hydroxy-3-[(tetrahydro-2H-pyran-4-yloxy)amino]propylcarbamate

1,3-benzodioxole-5-sulfonyl chloride

diisopropylethylamine

→

white crystals

Rendimiento 39.0%

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl 3-[(1,3-benzodioxol-5-ylsulfonyl)(tetrahydro-2H-pyran-4-yloxy)amino]-1-benzyl-2-hydroxypropylcarbamate

Rendimiento 39.0%

Disolventes

THF

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with 1N HCl, saturated sodium bicarbonate solution, brine
2. 2
   Secadowas dried over magnesium sulfate
3. 3
   ConcentraciónThe solution was concentrated under vacuum
4. 4
   Otrothe crude product was purified by silica gel chromatography (1:5 hexanes/ethyl acetate)
5. 5
   OtroThe purified oil was crystallized

Procedimiento

(3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-benzyl-2-hydroxy-3-[(tetrahydro-2H-pyran-4-yloxy)amino]propylcarbamate (0.23 mmol, 100 mg) was combined 1,3-benzodioxole-5-sulfonyl chloride (0.28 mmol, 61 mg), diisopropylethylamine (0.69 mmol, 0.12 mL) in anhydrous THF (2 mL) and allowed to stir 72 hours at room temperature under nitrogen. The reaction was diluted with ethyl acetate and washed with 1N HCl, saturated sodium bicarbonate solution, brine and was dried over magnesium sulfate. The solution was concentrated under vacuum and the crude product was purified by silica gel chromatography (1:5 hexanes/ethyl acetate). The purified oil was crystallized to provide 55 mg (39%) of white crystals. Rf=0.2 (1:5 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.38-7.13 (9H,m), 6.90 (1H,d), 6.10 (2H,s), 5.64 (1H,s), 5.02 (1H,m), 4.82 (1H,m), 4.41 (1H,m), 3.99-3.79 (6H,m), 3.72-3.59 (2H,m), 3.49-3.33 (2H,m), 3.25-2.51 (6H,m), 2.09-1.98 (2H,m), 1.69-1.43 (2H,m). MS (ESI): M+H=621.

Fuente