Reacción #6695

Ecuación de reacción

4′-(4-butoxybutoxy)-2′,3′-difluorobiphenyl-4-carboxylic acid

4′-(4-Butoxybutoxy)-2′,3′-difluorobiphenyl-4-carboxylic acid

4-hydroxybenzoic acid (R)-1-trifluoromethyl-heptyl ester

[R]-1-Trifluoromethylheptyl 4-Benzyloxybenzoate

DMAP

→

2′,3′-difluoro-4′-(4-pentyloxybutoxy)-biphenyl-4-carboxylic acid 4-[(R)-1-trifluoromethylheptyloxycarbonyl]-phenyl ester

Rendimiento 65.0%

2′,3′-Difluoro-4′-(4-pentyloxybutoxy)-biphenyl-4-carboxylic acid 4-[(R)-1-trifluoromethylheptyloxycarbonyl]-phenyl ester

Rendimiento 65.0%

Disolventes

THF

DIC

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with water
2. 2
   Extracciónextracted with ethyl acetate:hexane(1:1)
3. 3
   Lavadowashed with brine
4. 4
   Secadodried over MgSO4
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroPurification by chromatography on silica gel (5% EtOAc/hexanes)

Procedimiento

To a solution of 4′-(4-butoxybutoxy)-2′,3′-difluorobiphenyl-4-carboxylic acid (27) (1 equi.), (4-hydroxybenzoic acid (R)-1-trifluoromethyl-heptyl ester (13, Scheme 7) (1 equi.), and DMAP (dimethylaminopyridine) (0.1 equi.) in THF (25 mL/mmole), DIC (diisopropyl carbodiimide) (1.2 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane(1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) gave 2′,3′-difluoro-4′-(4-pentyloxybutoxy)-biphenyl-4-carboxylic acid 4-[(R)-1-trifluoromethylheptyloxycarbonyl]-phenyl ester (28) as a white solid (65%).

Fuente