Sodium Hydroxide → N-[3-((hydroxyimino)methyl)benzyl]succinamic acid tert-butyl ester

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Reaction Steps

A 3.2 M aqueous solution of sodium hydroxide (0.5 ml, 1.60 mmol) was added to a solution of N-(3-formylbenzyl)succinamic acid tert-butyl ester (312 mg, 1.07 mmol) and hydroxylamine hydrochloride (89 mg, 1.29 mmol) in ethanol (2.5 ml) and water (0.5 ml). The reaction mixture was stirred at room temperature for 3 days. A 10% aqueous solution of sodium hydrogensulphate (20 ml) and water (50 ml) were added. The mixture was extracted with ethyl acetate (3×50 ml). The combined organic layers were dried over magnesium sulphate. The solvent was removed in vacuo to give 249 mg of crude N-[3-((hydroxyimino)methyl)benzyl]succinamic acid tert-butyl ester, which was used without further purification in the next step.

Provenance & Evidence