Triethylamine → HCID 178468983, compound

Participants

Reaction Conditions

Reaction Steps

The above amine (0.315 g, 1.13 mmol) was dissolved in dry dimethylformamide (12 mL), cooled to 0° C. with an ice bath and then treated with 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (Aldrich, 0.493 g, 1.70 mmol), triethylamine (0.358 g, 3.50 mmol), and mercuric chloride (0.369 g, 1.36 mmol). The ice bath was removed and the reaction mixture was stirred under nitrogen at room temperature for 20 h. To the tan reaction mixture was added ethyl acetate (95 mL), and the mixture filtered through a bed of Celite®. The yellow filtrate was washed with water (50 mL), saturated sodium chloride (50 mL), and water (50 mL). The combined aqeuous layers were extracted with ethyl acetate (2×25 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated on a rotary evaporator. The crude yellow oil was purified by flash chromatography using 80% ethyl acetate/hexane to give 0.360 g (61%) of 1-{2-{[(tert-butoxycarbonylamino)(tert-butoxycarbonylimino)-methyl]amino}-4-ethoxycarbonylphenyl}-5-hydroxymethylpyrrolidin-2-one as a foamy, yellow solid, mp 104-110° C.

Provenance & Evidence