Reaktion #170997

Reaktionsgleichung

2-(4-aminophenoxy)-propionic acid methyl ester

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

triethylamine

benzyloxy acetyl chloride

→

51

Ausbeute 59.8%

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

Ausbeute 59.8%

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 51 was extracted into chloroform
5. 5
   Waschenwashed with 5% sodium bicarbonate (2×100 ml) and water (200 ml)
6. 6
   Trocknendried over sodium sulphate
7. 7
   workup.DISTILLATIONdistilled
8. 8
   SonstigeCrude 51 was purified by column chromatography on silica gel

Vorschrift

To a mixture of 2-(4-aminophenoxy)-propionic acid methyl ester 10 (20 grams, 102.5 mmol) and triethylamine (23 ml, 165 mmol) in acetone (120 ml) at 0° C. was added dropwise benzyloxy acetyl chloride (28 g, 152 mmol) followed by stirring at room temp for 12 hours. The solids were filtered off, acetone distilled off, and water (100 ml) added. Crude 51 was extracted into chloroform, washed with 5% sodium bicarbonate (2×100 ml) and water (200 ml), then dried over sodium sulphate and distilled. Crude 51 was purified by column chromatography on silica gel using benzene as eluant to get pure 51 (21 g, 59.8%) as a light brown powder with an m.p. between 67-70° C. IH NMR (CDCl3) δ 1.60 (d, 3H, CH3), 3.72 (s, 3H, Ester), 4.02 (s, 2H, CH2), 4.62 (s, 2H, CH2), 4.68 (q, 1H, CH), 6.76 (d, 2H, Ar), 7.30 (m, 5H, Ar), 7.42 (d, 2H, Ar), 8.18 (s, 1H, NH)

Quelle