Reacción #43958

Ecuación de reacción

hydrochloric acid

methyl [(3S)-6-({2′-(acetoxymethyl)-6′-methyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate

methanol

sodium hydroxide

→

title compound

Rendimiento 51.0%

[(3S)-6-({2′-(hydroxymethyl)-6′-methyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetic acid

Rendimiento 51.0%

Disolventes

water

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate
2. 2
   LavadoThe extract was washed with saturated brine
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=50:50-100:0) and preparative HPLC
6. 6
   Otrothe obtained crystals were recrystallized from heptane-ethyl acetate

Procedimiento

To a solution of methyl [(3S)-6-({2′-(acetoxymethyl)-6′-methyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate (1.11 g, 1.86 mmol) in a mixed solvent of methanol (4 mL) and tetrahydrofuran (8 mL) was added 2 M aqueous sodium hydroxide solution (2 mL), and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was diluted with water, acidified with 1 M hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=50:50-100:0) and preparative HPLC, and the obtained crystals were recrystallized from heptane-ethyl acetate to give the title compound (0.508 g, yield 51%) as colorless crystals.

Fuente