Reaktion #589047

Reaktionsgleichung

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

triethylamine

benzyloxy acetyl chloride

→

53

Ausbeute 22.2%

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

Ausbeute 22.2%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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 dropwise 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.

Quelle