HCID 20285448, compound → HCID 20285455, compound

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Reaction Steps

To N-(3-Acetylthio-2-methylpropanoyl)-N-cyclohexylglycine (5.1 g, 16.9 mol) was added 100 ml of ammonia-saturated methanol, and the resulting solution stirred for 2.5 hours at room temperature under nitrogen. The solution was concentrated and the residue dissolved in methanol and passed through a column of AG-50W-X2 cation exchange resin. Those fractions showing a positive nitroprusside test were combined and concentrated. This material was then purified by medium pressure liquid chromatography eluting with ethyl acetate/hexane/acetic acid, 48:48:2 to give 0.7 g of N-(3-mercapto-2-methylpropanoyl)-N-cyclohexylglycine as an oil. The compound was characterized as its DCHA salt, prepared by dissolving the acid in ether and adding DCHA to pH 9. The salt was isolated as a white crystalline solid, m.p. 158°-160°.

Provenance & Evidence