Reaction #2045046

Reaction equation

1,3-dicyclohexylcarbodiimide

4-aminophenoxyacetic acid methyl ester

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

benzyloxyacetic acid

→

66

Yield 68.9%

4-(2-Benzyloxyacetylamino)phenoxyacetic acid methyl ester

Yield 68.9%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   FiltrationThe solids were filtered off
2. 2
   Washthe dichloromethane solution was washed with 5% sodium bicarbonate solution (100 ml), water (100 ml)
3. 3
   Dryingdried over sodium sulphate
4. 4
   workup.DISTILLATIONdistilled
5. 5
   Otherto get crude 66
6. 6
   OtherThe crude 66 was purified by column chromatography on silica gel

Procedure

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.

Source