反応 #2045050

反応方程式

Benzyloxyacetyl chloride

6-(4-aminophenoxy)hexanoic acid methyl ester

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

triethylamine

→

70

収率 22.2%

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

収率 22.2%

溶媒

acetone

反応条件

後処理

1. 1
   ろ過Solids were filtered off
2. 2
   workup.DISTILLATIONacetone distilled off
3. 3
   workup.ADDITIONwater (100 ml) added
4. 4
   抽出Crude 70 was extracted into chloroform
5. 5
   洗浄washed with 5% sodium bicarbonate solution (2×100 ml), water (100 ml)
6. 6
   乾燥dried over sodium sulphate
7. 7
   workup.DISTILLATIONdistilled
8. 8
   その他Crude 70 was purified by column chromatography on silica gel

実験手順

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.

出典