Reacción #76076

Ecuación de reacción

2-ethoxy-3-{4-[2-(1-heptyl-3-p-tolyl-ureido)-ethyl]-phenyl}-propionic acid methyl ester

LiOH

→

2-ethoxy-3-{4-[2-(1-heptyl-3-p-tolyl-ureido)-ethyl]-phenyl}-propionic acid

Rendimiento 82.3%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solution was quenched by the addition of 2 N HCl until the solution
2. 2
   ExtracciónAfter dilution with twice its volume in water, the aqueous layer was extracted with diethyl ether (2×)
3. 3
   Lavadowashed with 2 M HCl (2×)
4. 4
   Secadodried over anhydrous sodium sulfate
5. 5
   Concentraciónconcentrated to a crude oil
6. 6
   OtroThe crude oil was chromatographed on silica gel (2% methanol/methylene chloride gradient to 15% methanol/methylene chloride)

Procedimiento

A solution of 2-ethoxy-3-{4-[2-(1-heptyl-3-p-tolyl-ureido)-ethyl]-phenyl}-propionic acid methyl ester (40 mg, 0.083 mmol) and 1 M LiOH (0.25 mmol, 0.25 mL) in tetrahydrofuran (2 mL) was allowed to stir at room temperature for 16 hours. The solution was quenched by the addition of 2 N HCl until the solution had a pH<2. After dilution with twice its volume in water, the aqueous layer was extracted with diethyl ether (2×). The organic layers were combined, washed with 2 M HCl (2×), dried over anhydrous sodium sulfate, and concentrated to a crude oil. The crude oil was chromatographed on silica gel (2% methanol/methylene chloride gradient to 15% methanol/methylene chloride) to give 2-ethoxy-3-{4-[2-(1-heptyl-3-p-tolyl-ureido)-ethyl]-phenyl}-propionic acid as a white waxy-solid (32 mg, 82%).

Fuente