Hydrochloric Acid → Methyl 1-(4-methoxyphenylsulfonamido)cyclohexanecarboxylate

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Reaction Steps

1-Amino-cyclohexanecarboxylic acid methyl ester hydrochloride (32 g, 165 mmol) was suspended in DCM (1000 ml), and diisopropylethylamine (84.9 ml, 496 mmol) was added thereto. A solution of 4-methoxybenzenesulfonyl chloride (51.2 g, 248 mmol) dissolved in DCM (150 ml) was added dropwise at 0° C., and stirring was carried out overnight at room temperature. Aqueous 1 M HCl (150 ml) and water (50 ml) were added and the phases were separated. The organic phase was dried over sodium sulfate and concentrated to dryness. The product was purified by column chromatography on silica gel (DCM/methanol 99:1).

Provenance & Evidence