Reaction #78201

Reaction equation

benzyl (4R)-4-t-butoxycarbonylamino-5-chloropentanoate

3-hydroxy-4-iodobenzonitrile

potassium carbonate

potassium iodide

→

title compound

Benzyl (4R)-4-t-butoxycarbonylamino-5-(5-cyano-2-iodophenoxy)pentanoate

Solvents

DMF

Conditions

Workup

1. 1
   OtherThe solvent was evaporated
2. 2
   Otherthe crude product obtained by an ordinary method with ethyl acetate as the extracting solvent
3. 3
   Otherwas purified by the silica gel chromatography (ethyl acetate/hexane)

Procedure

8.29 g (24.3 mmol) of benzyl (4R)-4-t-butoxycarbonylamino-5-chloropentanoate, 6.9 g (28.0 mmol) of 3-hydroxy-4-iodobenzonitrile, 6.9 g (50 mmol) of potassium carbonate and 4.15 g (25 mmol) of potassium iodide were stirred together in 80 ml of DMF at 70° C. for 3 days. The solvent was evaporated, and the crude product obtained by an ordinary method with ethyl acetate as the extracting solvent was purified by the silica gel chromatography (ethyl acetate/hexane) to obtain the title compound.

Source