Réaction #2045048

Équation de réaction

Benzyloxyacetyl chloride

2-(4-aminophenoxy)propionic acid methyl ester

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

triethylamine

→

68

Rendement 59.8%

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

Rendement 59.8%

Solvants

acetone

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source