Oxalyl chloride → (trans)-N-Hydroxy-2-[(4-Phenoxybenzenesulfonyl)amino]cyclohexane-carboxamide

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Reaction Steps

A solution of the acid obtained in Example 7 (1.00 g, 2.66 mmol) was reacted with oxalyl chloride (2M solution in CH2Cl2, 6.65 mL, 13.3 mmol) followed by O-(trimethylsilyl)hydroxylamine (2.8 g, 26.64 mmol) as described in Example 2 to obtain 0.48 g (46%) of the desired product. The melting point was 182-184° C. Mass spectrometry revealed a molecular ion (MH)+ peak at m/z 391. Proton NMR analysis in CDCl3 resulted in the following chemical shifts (δ): 0.98-1.96 (m, 8H, cyclohexyl methylenes), 2.05-2.16 (m, 1H, C-1H), 3.50-3.67 (broad hump, 1H, C-2H), 6.15 (broad hump, 1H, SO2NH), 7.01-7.88 (m, 9H, aryl-H), and 8.98 (broad s, 1H, CONH).

Provenance & Evidence