반응 #2045046

반응 방정식

1,3-dicyclohexylcarbodiimide

4-aminophenoxyacetic acid methyl ester

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

benzyloxyacetic acid

→

66

수율 68.9%

4-(2-Benzyloxyacetylamino)phenoxyacetic acid methyl ester

수율 68.9%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   여과The solids were filtered off
2. 2
   세척the dichloromethane solution was washed with 5% sodium bicarbonate solution (100 ml), water (100 ml)
3. 3
   건조dried over sodium sulphate
4. 4
   workup.DISTILLATIONdistilled
5. 5
   기타to get crude 66
6. 6
   기타The crude 66 was purified by column chromatography on silica gel

실험 절차

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.

출처