3-Chloro-6-[2-(3-chloro-4-isopropoxy-phenyl)-ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-one → 6-[2-(3-Chloro-4-isopropoxy-phenyl)-ethyl]-3-(5-chloro-1-isopropyl-1H-benzoimidazol-2-ylsulfanyl)-6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-one

Participants

Reaction Steps

The title compound was prepared analogously to Example C(4), where 3-Chloro-6-[2-(3-chloro-4-isopropoxy-phenyl)-ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-one (from Step 1 below) was substituted in place of 3-Chloro-6-(2-cyclohex-1-enyl-ethyl)-6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-one and 5-Chloro-1-isopropyl-2-mercapto benzimidazole was substituted in place of 5-Pyridin-4-yl-4H-[1,2,4]triazole-3-thiol of that example. 1H NMR (DMSO-d6): δ 1.13 (d, J=6.1 Hz, 6H), 1.41 (d, J=7.1 Hz, 6H), 1.42-1.8 (m, 10H), 2.08-2.13 (m, 1H), 2.43-2.54 (m 3H), 2.79 (d, J=17.0, 1H), 4.44-4.48 (m, 1H), 4.63-4.69 (m, 1H), 6.89-6.91 (m, 2H), 6.95-7.00 (m, 2H), 7.14 (s, 1H), 7.49 (d, J=8.6 Hz, 1H), 12.0 (brs, 1H); Anal. Calcd. For C31H36Cl2N2O4S.1.0AcOH: C, 59.72; H, 6.07; N, 4.22; Found: C, 59.50; H, 6.16; N, 4.33. ESIMS (MH+): 604.

Provenance & Evidence