Diisopropylethylamine → HCID 59162872, compound

Participants

Reaction Steps

To a stirred solution of (2S,3R)-3-(4-nitro-benzoyloxy)-pyrrolidine-2-carboxylic acid methy ester hydrochloride salt prepared by Method C followed by Method F (109 mg, 0.33 mmol), 4-methoxy-3-trifluoromethylsulfanyl-benzoic acid (76.6 mg, 0.30 mmol), in anhydrous dioxane (2.0 mL) was added HATU (136 mg, 0.36 mmol) and DIEA (205 μL, 1.2 mmol) with rapid stirring. The reaction mixture was stirred 2 h at rt then diluted with 50% aq. hydroxylamine (2.0 mL) and stirred an additional 17 h. The crude reaction mixture was purified by preparative reverse phase HPLC to furnish the product (2S,3R)-3-hydroxy-N-hydroxy-1-(4-methoxy-3-trifluoromethylsulfanyl-benzoyl)-pyrrolidine-2-carboxamide (4.0 mg, 4% yield). HPLC: Rt=4.050 min following Method HH; ES−MS: calcd. for C14H15F3N2O5S (380.07). Found: 379.0 [M−H].

Provenance & Evidence