Reacción #595262

Ecuación de reacción

tert-butyl 3-(2-fluoro-4-{[(4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methyl][(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

tetrahydro-2H-thiopyran-4-ol

triphenylphosphine

diethyl azodicarboxylate

tetrahydro-2H-thiopyran-4-ol

triphenylphosphine

diethyl azodicarboxylate

→

title compound

Rendimiento 100.7%

tert-butyl 3-(4-{{[2′,6′-dimethyl-4′-(tetrahydro-2H-thiopyran-4-yloxy)biphenyl-3-yl]methyl}[(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate

Rendimiento 100.7%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred for 16 hr
2. 2
   workup.STIRRINGwas further stirred for 8 hr
3. 3
   ConcentraciónThe reaction mixture was concentrated under reduced pressure
4. 4
   Otrothe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1)

Procedimiento

To a solution of tert-butyl 3-(2-fluoro-4-{[(4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methyl][(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (3.0 g, 4.73 mmol), tetrahydro-2H-thiopyran-4-ol (0.62 g, 5.20 mmol) and triphenylphosphine (1.36 g, 5.20 mmol) in tetrahydrofuran (60 mL) was added diethyl azodicarboxylate (40% toluene solution, 2.79 mL, 6.15 mmol) under stirring at room temperature, and the mixture was stirred for 16 hr. To the reaction mixture were added reagents (tetrahydro-2H-thiopyran-4-ol, triphenylphosphine and diethyl azodicarboxylate) in a half amount as mentioned above, and the mixture was further stirred for 8 hr. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1) to give the title compound (3.5 g, yield 100%) as a pale-yellow oil.

Fuente