Reaction #725903

Reaction equation

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

(4-Isocyanato-phenoxy)-acetic acid methyl ester

→

30

Yield 56.5%

{4-[2-(4-Methoxycarbonylmethoxy-phenylcarbamoyloxy)-ethoxycarbonylamino]-phenoxy}-acetic acid methyl ester

Yield 56.5%

Solvents

toluene

Conditions

Workup

1. 1
   workup.DISTILLATIONToluene was distilled off
2. 2
   workup.ADDITIONwater (10 ml) was added
3. 3
   ExtractionCrude 30 was extracted into chloroform
4. 4
   Dryingdried over sodium sulphate
5. 5
   workup.DISTILLATIONdistilled
6. 6
   Otherpurified by column chromatography on silica gel

Procedure

To [4-(2-Hydroxy-ethoxycarbonylamino)-phenoxy]-acetic acid methyl ester 29 (1 g, 3.72 mmol) in toluene (10 ml) was added (4-Isocyanato-phenoxy)-acetic acid methyl ester 28 (0.8 g, 3.8 mmol) at room temperature and heated to 50° C. for 20 hours. Toluene was distilled off and water (10 ml) was added. Crude 30 was extracted into chloroform, dried over sodium sulphate, distilled and purified by column chromatography on silica gel using chloroform as eluant to get pure 30 (1 g, 56.5%) as a white fluffy powder.

Source