Tetrahydrofuran → HCID 21997017, compound

Participants

Reaction Steps

A mixture of 2-(4-methoxybenzenesulfonylmethyl)-3-(4-methoxybenzenesulfonyl)-propionic acid (5.0 g, 12 mmol) in tetrahydrofuran (30 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.3 g, 23 mmol), benzylhydroxylamine hydrochloride (2.3 g, 14 mmol), and distilled water (30 mL) is stirred overnight. The mixture is filtered to yield a white precipitate which is dissolved in chloroform (200 ml) and filtered. The filtrate is extracted with brine (100 mL) and the organic phase concentrated in vacuo, to yield N-benzyloxy-2-(4-methoxybenzenesulfonylmethyl)-3-(4-methoxybenzenesulfonyl)-propionamide (2.24 g, 36%). The initial filtrate from the overnight reaction is transferred to ethyl acetate and extracted with 10% hydrochloric acid, water, aqueous sodium bicarbonate, and brine, and concentrated in vacuo to also yield the title compound as a white solid.

Provenance & Evidence