반응 #170999

반응 방정식

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

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

triethylamine

benzyloxy acetyl chloride

→

53

수율 22.2%

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

수율 22.2%

용매

acetone

반응 조건

후처리

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

실험 절차

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.

출처