Trifluoroacetic acid → HCID 66559224, compound

Participants

Reaction Steps

To a solution of (2R)-2-methyl-4-(5-methyl-4-phenyl-1H-1,2,3-triazol-1-yl)-2-(methylsulfonyl)butanoic acid and (2R)-2-methyl-4-(4-methyl-5-phenyl-1H-1,2,3-triazol-1-yl)-2-(methylsulfonyl)butanoic acid (115 mg, 0.341 mmol, 1 eq) in THF (5 mL) was added N-methyl morpholine (65.5 mg, 0.341 mmol, 1 eq), and CDMT (59.9 mg, 0.341 mmol, 1 eq). The reaction mixture was allowed to stir at RT for 1 h then O-tetrahydro-2H-pyran-2-yl-hydroxylamine (39.9 mg 0.341 mmol, 1 eq) was added and the reaction mixture was allowed to stir at RT for 2 days. Upon completion of the coupling reaction (as observed by LC-MS monitoring), 1 mL of TFA was added and the mixture was allowed to stir at RT for 3 h. The reaction mixture was concentrated and purified by HPLC to give (2R)—N-hydroxy-2-methyl-4-(5-methyl-4-phenyl-1H-1,2,3-triazol-1-yl)-2-(methylsulfonyl)butanamide (14 mg) as a 10:1 mixture with the corresponding regioisomer (2R)—N-hydroxy-2-methyl-4-(4-methyl-5-phenyl-1H-1,2,3-triazol-1-yl)-2-(methylsulfonyl)butanamide. 1H NMR (400 MHz, METHANOL-d4) δ 7.61-7.67 (m, 2H), 7.43-7.50 (m, 2H), 7.38 (d, J=7.42 Hz, 1H), 4.51-4.63 (m, 1H), 4.36-4.48 (m, 1H), 3.06 (s, 3H), 2.85-2.93 (m, 1H), 2.51 (s, 3H), 2.43 (ddd, J=13.42, 10.10, 5.37 Hz, 1H), 1.72 (s, 3H). LC-MS M+H+353.1.

Provenance & Evidence