Reaction #2045048

Reaction equation

Benzyloxyacetyl chloride

2-(4-aminophenoxy)propionic acid methyl ester

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

triethylamine

→

68

Yield 59.8%

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

Yield 59.8%

Solvents

acetone

Conditions

Workup

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
   Washwashed with 5% sodium bicarbonate (2×100 ml), water (200 ml)
6. 6
   Dryingdried over sodium sulphate
7. 7
   workup.DISTILLATIONdistilled
8. 8
   OtherCrude 68 was purified by column chromatography on silica gel

Procedure

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