Benzoyl chloride → N-hydroxy-7-(4-methoxyphenyl)-7-oxoheptanamide

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Reaction Steps

Following the procedure described in Example 18, step 1, 2, 3, but substituting respectively ethyl-6-iodohexanoate for ethyl-7-iodoheptanoate and 4-methoxybenzoyl chloride for benzoyl chloride, and then the resulting carboxylic acid was substituted for 37 in Example 14, step 3, using 1.1 equivalent of NH2OH.HCl and triethylamine each, to afford the title compound 110 in 54% yield. 1H NMR (300 MHz, 20% CD3OD in CDCl3): δ 7.86 (d, J=8.7 Hz, 2H), 6.88 (d, J=8.7 Hz, 2H), 3.81 (s, 3H), 2.87 (t, J=6.6 Hz, 2H), 2.07 (br t, 2H), 1.62 (m, 4H), 1.34 (m, 2H). 13C NMR (75 MHz, 20% CD3OD in CDCl3): δ 23.68, 24.96, 28.32, 32.28, 37.63, 55.14, 113.49, 129.48, 130.13, 163.35, 171.06, 199.81.

Provenance & Evidence