Реакция #2045050

Уравнение реакции

Benzyloxyacetyl chloride

6-(4-aminophenoxy)hexanoic acid methyl ester

6-(4-Amino-phenoxy)-hexanoic acid methyl ester

triethylamine

→

70

Выход 22.2%

6-[4-(2-Benzyloxyacetylamino)phenoxy]hexanoic acid methyl ester

Выход 22.2%

Растворители

acetone

Условия реакции

Обработка

1. 1
   ФильтрацияSolids were filtered off
2. 2
   workup.DISTILLATIONacetone distilled off
3. 3
   workup.ADDITIONwater (100 ml) added
4. 4
   ЭкстракцияCrude 70 was extracted into chloroform
5. 5
   Промывкаwashed with 5% sodium bicarbonate solution (2×100 ml), water (100 ml)
6. 6
   Сушкаdried over sodium sulphate
7. 7
   workup.DISTILLATIONdistilled
8. 8
   ДругоеCrude 70 was purified by column chromatography on silica gel

Методика

Benzyloxyacetyl chloride (25 gm, 135.5 mmol) was added dropwise to a mixture of 6-(4-aminophenoxy)hexanoic acid methyl ester 21 (25 g, 105 mmol) and triethylamine (21.4 g, 211.6 mmol) in acetone (200 ml) at 0° C. and stirred at room temp. for 12 hrs. Solids were filtered off, acetone distilled off and water (100 ml) added. Crude 70 was extracted into chloroform, washed with 5% sodium bicarbonate solution (2×100 ml), water (100 ml), dried over sodium sulphate and distilled. Crude 70 was purified by column chromatography on silica gel using benzene as eluant to get pure 70 (9 g, 22.2%) as a off-white powder. M.p: 46-49° C.

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