Water → N-(3-Acetylthio-2-methylpropanoyl)-N-cyclopentylglycine

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Reaction Steps

A mixture containing 80.1 g (0.23 mol) of N-(3-acetylthio-2-methyl-propanoyl)-N-cyclopentyl glycine t-butyl ester, 37.9 g (0.35 mol) of trimethysilyl chloride, and 52.5 g (0.35 mol) of sodium iodide in 300 ml of acetonitrile was heated between 45°-50° C. for 30 minutes. Following the addition of 50 ml of water, the mixture was concentrated in vacuo. The residue was rendered basic with 400 ml of saturated aqueous NaHCO3, washed three times with ethyl acetate, acidified with concentrated HCl, and extracted three times with ethyl acetate. These later organic extracts were combined, dried over MgSO4, filtered, and concentrated in vacuo to afford 60 g (91%) of the crude product. Purification via high pressure liquid chromatography (HPLC) [ethyl acetate/hexane/acetic acid (60/40/2)] afforded N-(3-acetylthio-2-methylpropanoyl)-N-cyclopentyl glycine as an oil.

Provenance & Evidence