Reacción #2045048

Ecuación de reacción

Benzyloxyacetyl chloride

2-(4-aminophenoxy)propionic acid methyl ester

2-(4-Amino-phenoxy)-propionic acid methyl ester

triethylamine

→

68

Rendimiento 59.8%

2-[4-(2-Benzyloxyacetylamino)phenoxy]propionic acid methyl ester

Rendimiento 59.8%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónSolids were filtered off
2. 2
   workup.DISTILLATIONacetone distilled off
3. 3
   workup.ADDITIONwater (100 ml) added
4. 4
   ExtracciónCrude 68 was extracted into chloroform
5. 5
   Lavadowashed with 5% sodium bicarbonate (2×100 ml), water (200 ml)
6. 6
   Secadodried over sodium sulphate
7. 7
   workup.DISTILLATIONdistilled
8. 8
   OtroCrude 68 was purified by column chromatography on silica gel

Procedimiento

Benzyloxyacetyl chloride (28 g, 152 mmol) was added dropwise to a mixture of 2-(4-aminophenoxy)propionic acid methyl ester 18 (20 g, 102.5 mmol) and triethylamine (23 ml, 165 mmol) in acetone (120 ml) at 0° C. and stirred at room temperature for 12 hrs. Solids were filtered off, acetone distilled off and water (100 ml) added. Crude 68 was extracted into chloroform, washed with 5% sodium bicarbonate (2×100 ml), water (200 ml), dried over sodium sulphate and distilled. Crude 68 was purified by column chromatography on silica gel using benzene as eluant to get pure 68 (21 g, 59.8%) as a light brown powder. M.p: 67-70° C.

Fuente