Water → HCID 86684917, compound

Participants

Reaction Steps

Benzenesulfonic acid (3S,5S)-5-(1-cyano-cyclopropylcarbamoyl)-1-(1-trifluoromethyl-cyclopropanecarbonyl)-pyrrolidin-3-yl ester (225 g, 477 mmol) was dissolved in dimethylacetamide (1.125 L) and potassium carbonate (166.5 g, 1.193 mol) was added. At room temperature, a solution of 2-chloro-4-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzenethiol (142 g, 553.2 mmol) in tetrahydrofuran (135 mL) was added slowly, keeping the internal temperature below 29° C. (ice bath cooling necessary). The mixture was stirred for 5.5 h at room temperature. After addition of ice (700 g) and water (2 L), the mixture was extracted with tert-butyl-methylether (1×1.5 L, 3×750 mL). The combined organic extracts were washed with brine (450 mL) and concentrated in vacuo to yield the title compound as a brown viscous oil (300.4 g). The crude product (containing dimethylacetamide) was used in the next step without further purification.

Provenance & Evidence