Реакция #2045046

Уравнение реакции

1,3-dicyclohexylcarbodiimide

4-aminophenoxyacetic acid methyl ester

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

benzyloxyacetic acid

→

66

Выход 68.9%

4-(2-Benzyloxyacetylamino)phenoxyacetic acid methyl ester

Выход 68.9%

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   ФильтрацияThe solids were filtered off
2. 2
   Промывкаthe dichloromethane solution was washed with 5% sodium bicarbonate solution (100 ml), water (100 ml)
3. 3
   Сушкаdried over sodium sulphate
4. 4
   workup.DISTILLATIONdistilled
5. 5
   Другоеto get crude 66
6. 6
   ДругоеThe crude 66 was purified by column chromatography on silica gel

Методика

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.

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