5-(Chloromethyl)-3-ethyl-1,2,4-oxadiazole → 6-[2-(5-Chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyl-3-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-4-hydroxy-5,6-dihydro-2H-pyran-2-one

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Reaction Steps

The title compound was prepared as described in Example B(53), using 5-(chloromethyl)-3-ethyl-1,2,4-oxadiazole (Step 1, below) in place of 5-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazole, and using 6-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione in place of 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione. Yield: 7%. 1H NMR (300 MHz, DMSO-d6) δ 1.10 (t, J=7.8 Hz, 3H), 1.25-1.73 (m, 8H), 1.89 (m, 2H), 2.33 (m, 1H), 2.43-2.53 (m, 2H, overlap with DMSO-d5), 2.58 (q, m, overlap, 3H), 2.76 (d, J=18 Hz, 1H), 3.75 (ABQ pattern, J=16 Hz, 2H), 3.77 (s, 3H), 3.84 (s, 3H), 6.71 (s, 1H), 7.10 (s, 1H), 11.31 (br s, 1H). LC-MS (APCI) calcd for C25H31ClN2O6: 490.19; found (M+H+) 491.0 m/z.

Provenance & Evidence