(-)-Terconazole

Example 20: (2S,4R) -(-)-1-[4-[[2-(2,4-dichlorophenyl)-2-[(1H-1,2,4-triazol-1-yl]methyl-1,3-dioxolane-4-yl]methoxy]phenyl]-4-(1-methylethyl)piperazine, (2S,4R) - (-)-terconazole.

This compound is prepared following the process described for (+)-torconazole, starting from (2S,4S)-(-)-IV (Ar = 2,4-dichlorophenyl, Y = N, R = CH₃) (224 mg, 0.55 mmol), 4-(4-hydroxyphenyl)-1-(1-methylethyl)-piperazine (121 mg, 0.55 mmol), NaH (22.4 mg, 0.56 mmol) in 8 ml of DMSO. (2S,4R) -(-(-terconazole ((2S,4R)-V, Ar

= 2,4-dichlorophenyl, Y = N, Z = CH(CH₃)₂) is obtained as a white solid, m.p. 76-78ºC, [α]_D ²⁰= -12.0 (c = 0.4.

CHCl₃).

http://www.google.com/patents/WO1996029325A1?cl=en