Reaktion #2045048

Reaktionsgleichung

Benzyloxyacetyl chloride

2-(4-aminophenoxy)propionic acid methyl ester

2-(4-Amino-phenoxy)-propionic acid methyl ester

triethylamine

→

68

Ausbeute 59.8%

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

Ausbeute 59.8%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationSolids were filtered off
2. 2
   workup.DISTILLATIONacetone distilled off
3. 3
   workup.ADDITIONwater (100 ml) added
4. 4
   ExtraktionCrude 68 was extracted into chloroform
5. 5
   Waschenwashed with 5% sodium bicarbonate (2×100 ml), water (200 ml)
6. 6
   Trocknendried over sodium sulphate
7. 7
   workup.DISTILLATIONdistilled
8. 8
   SonstigeCrude 68 was purified by column chromatography on silica gel

Vorschrift

Benzyloxyacetyl chloride (28 g, 152 mmol) was added dropwise to a mixture of 2-(4-aminophenoxy)propionic acid methyl ester 18 (20 g, 102.5 mmol) and triethylamine (23 ml, 165 mmol) in acetone (120 ml) at 0° C. and stirred at room temperature for 12 hrs. Solids were filtered off, acetone distilled off and water (100 ml) added. Crude 68 was extracted into chloroform, washed with 5% sodium bicarbonate (2×100 ml), water (200 ml), dried over sodium sulphate and distilled. Crude 68 was purified by column chromatography on silica gel using benzene as eluant to get pure 68 (21 g, 59.8%) as a light brown powder. M.p: 67-70° C.

Quelle