Реакция #170999

Уравнение реакции

6-(4-aminophenoxy)-hexanoic acid methyl ester

6-(4-Aminophenoxy)-hexanoic acid methyl ester

triethylamine

benzyloxy acetyl chloride

→

53

Выход 22.2%

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

Выход 22.2%

Растворители

acetone

Условия реакции

Обработка

1. 1
   ФильтрацияThe solids were filtered off
2. 2
   workup.DISTILLATIONacetone distilled off
3. 3
   workup.ADDITIONwater (100 ml) added
4. 4
   ЭкстракцияCrude 53 was extracted into chloroform
5. 5
   Промывкаwashed with 5% sodium bicarbonate solution (2×100 ml)
6. 6
   Сушкаwater (100 ml), dried over sodium sulphate
7. 7
   workup.DISTILLATIONdistilled
8. 8
   ДругоеCrude 53 was purified by column chromatography on silica gel

Методика

To a mixture of 6-(4-aminophenoxy)-hexanoic acid methyl ester 17 (25 g, 105 mmol) and triethylamine (21.4 g, 211.6 mmol) in acetone (200 ml) at 0° C. was added drop-wise benzyloxy acetyl chloride (25 g, 135.5 mmol) followed by stirring at room temp. for 12 hrs. The solids were filtered off, acetone distilled off and water (100 ml) added. Crude 53 was extracted into chloroform, washed with 5% sodium bicarbonate solution (2×100 ml), then water (100 ml), dried over sodium sulphate and distilled. Crude 53 was purified by column chromatography on silica gel using benzene as eluant to get pure 53 (9 g, 22.2%), an off-white powder with a m.p. between 46-49° C.

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