Trifluoroacetic acid → HCID 135507290, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazine-2-carboxylic acid tert-butoxy-amide (318.3 mg, 0.609 mol) in methylene chloride (2.3 mL) was treated with trifluoroacetic acid (4.6 mL) and stirred at 25° C. overnight, then at 40° C. for 10–11 h, followed by stirring again at 25° C. overnight. The reaction solution was then concentrated in vacuo. Reverse phase high-performance liquid chromatography (Rainin Dynamax system, 60 Å C-18 column, l=214 nm, 50 mL/min of 50–100% acetonitrile with 0.1% trifluoroacetic acid/water with 0.1% trifluoroacetic acid over 55 min) afforded 5-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazine-2-carboxylic acid hydroxyamide (90.0 mg, 32%) as a pink foam: mp 134–139° C. (foam to gel); (ES)+-HRMS m/e calcd for C20H23ClN4O5S (M+H)+ 467.1151, found 467.1155.

Provenance & Evidence