Reacción #2045046

Ecuación de reacción

1,3-dicyclohexylcarbodiimide

4-aminophenoxyacetic acid methyl ester

(4-Amino-phenoxy)-acetic acid methyl ester

benzyloxyacetic acid

→

66

Rendimiento 68.9%

4-(2-Benzyloxyacetylamino)phenoxyacetic acid methyl ester

Rendimiento 68.9%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe solids were filtered off
2. 2
   Lavadothe dichloromethane solution was washed with 5% sodium bicarbonate solution (100 ml), water (100 ml)
3. 3
   Secadodried over sodium sulphate
4. 4
   workup.DISTILLATIONdistilled
5. 5
   Otroto get crude 66
6. 6
   OtroThe crude 66 was purified by column chromatography on silica gel

Procedimiento

To a mixture of 4-aminophenoxyacetic acid methyl ester 15 (20 g, 110.5 mmol) and benzyloxyacetic acid (20.4 g, 123 mmol) in anhydrous dichloromethane (200 ml) under nitrogen atm. was added dropwise a solution of 1,3-dicyclohexylcarbodiimide (63.2 g, 306 mmol) in anhydrous dichloromethane (80 ml). The reaction mixture was stirred at room temp. for 12 hrs. The solids were filtered off, the dichloromethane solution was washed with 5% sodium bicarbonate solution (100 ml), water (100 ml), dried over sodium sulphate, and distilled to get crude 66. The crude 66 was purified by column chromatography on silica gel using benzene as eluant to get pure 66 (25 g, 68.9%) as a white powder. M.p: 76-77.5° C.

Fuente