Réaction #2045026

Équation de réaction

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

6-[4-(2-Hydroxy-ethoxycarbonylamino)-phenoxy]-hexanoic acid methyl ester

6-(4-Isocyanatophenoxy)hexanoic acid methyl ester

6-(4-Isocyanato-phenoxy)-hexanoic acid methyl ester

→

38

Rendement 95.0%

6-(4-{2-[4-(5-Methoxycarbonyl-pentyloxy)-phenylcarbamoyloxy]-ethoxycarbonylamino}-phenoxy)-hexanoic acid methyl ester

Rendement 95.0%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   workup.DISTILLATIONToluene was distilled off
2. 2
   workup.ADDITIONwater (50 ml) was added
3. 3
   FiltrationThe solid was filtered
4. 4
   Autredried
5. 5
   Autreto give crude 38, which
6. 6
   Autrewas purified by column chromatography on silica gel

Mode opératoire

To a mixture of 6-[4-(2-Hydroxyethoxycarbonylamino)phenoxy]hexanoic acid methyl ester 37 (5 g, 15.38 mmol) in toluene (50 ml) was added 6-(4-Isocyanatophenoxy)hexanoic acid methyl ester 36 (4 g, 15.2 mmol) at room temperature and heated to 60° C. for 2 hours. Toluene was distilled off and water (50 ml) was added. The solid was filtered and dried to give crude 38, which was purified by column chromatography on silica gel using chloroform as eluant to get pure 38 (8.5 g, 94%) as a white powder. M.p: 118-120.5° C.

Source