Reaction #2045023

Reaction equation

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

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

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

→

34

Yield 61.8%

2-(4-{2-[4-(1-Methoxycarbonyl-ethoxy)-phenylcarbamoyloxy]-ethoxycarbonylamino}-phenoxy)-propionic acid methyl ester

Yield 61.8%

Solvents

toluene

Conditions

Workup

1. 1
   workup.DISTILLATIONToluene was distilled off
2. 2
   workup.ADDITIONwater (50 ml) was added
3. 3
   FiltrationThe solids were filtered
4. 4
   Otherdried
5. 5
   Otherto give crude 34, which
6. 6
   Otherwas purified by column chromatography on silica gel

Procedure

To 2-[4-(2-Hydroxyethoxycarbonylamino)phenoxy]propionic acid methyl ester 33 (5 g, 17.66 mmol) in toluene (50 ml) was added 2-(4-Isocyanato-phenoxy)-propionic acid methyl ester 32 (3.9 g, 17.64 mmol) at room temperature and heated to 60° C. for 30 hours. Toluene was distilled off and water (50 ml) was added. The solids were filtered and dried to give crude 34, which was purified by column chromatography on silica gel using chloroform as eluant to get pure 34 (5.5 g, 61.8%) as a white powder. M.p: 98-100° C.

Source