4-Methoxybenzenesulfonyl chloride → HCID 18678868, compound

Participants

Reaction Steps

To a solution of β-alanine ethyl ester (154 mg, 1 mmol) in anhydrous methylene chloride (7 mL) at room temperature was added triethyl amine (101 mg, 1 mmol) and 4-chlorobenzaldehyde (155 mg, 1.1 mmol). After being stirred for 0.5 h, sodium triacetoxyborohydride (318 mg, 1.5 mmol) was added and the reaction mixture was stirred for additional 1 h at room temperature, followed by the addition of 4-methoxybenzenesulfonyl chloride (207 mg, 1 mmol) and triethyl amine (152 mg, 1.5 mmol). The resulting mixture was stirred for 18 h, quenched with 10% citric acid (10 mL) and, after 30 min, extracted with methylene chloride (2×30 mL). Two phases was separated and the organic layers was washed with brine, dried over MgSO4, filtered, and concentrated. The crude product was purified by silica gel chromatography (2/1: hexanes/ethyl acetate) to give ethyl 3-[(4-chlorobenzyl)-(4-methoxybenzenesulfonyl)-amino]-propionate (44 mg, 0.1 mmol).

Provenance & Evidence