Hydroxylamine → 6-(4-((4-Chlorobenzyl)-methylamino)-benzenesulfinyl)-hexanoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of the 6-(4-((4-chlorobenzyl)-methylamino)-benzenesulfinyl)-hexanoic acid methyl ester (1.6 g, 4.0 mmol) in distilled THF (25 mL) containing 50% aqueous hydroxylamine (2.6 mL, 40 mmol) was added at 0° C. a solution of potassium hydroxide in methanol (1M, 8 mL, 8 mmol) in a dropwise manner. After stirring at 0° C. for 1 h, distilled water (25 mL) was added and the mixture was made neutral by dropwise addition of concentrated hydrochloric acid (10 M) at 0° C. The aqueous solution was extracted with ethyl acetate (2×50 mL) and the combined extracts were washed with brine (100 mL), dried over anhydrous MgSO4, filtered and evaporated to dryness. The solid residue was recrystallised from acetone/40-60° C. petroleum ether to give the title compound (867 mg, 53%) as a white powder, mp 109-111° C.

Provenance & Evidence