Triethylamine hydrochloride → HCID 86607921, compound

Participants

Reaction Steps

According to the procedure of Example 56, Step 4, methyl (1S,2R)-1-(hydroxymethyl) -2-[methyl({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylate (213 mg, 0.439 mmol), 5M sodium hydroxide solution (0.44 mL), and triethylamine hydrochloride (365 mg, 2.63 mmol) provided methyl (1S,2R)-1-(hydroxymethyl)-2-[methyl({4-[(2-methylquinolin -4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid. To the acid was added BOP (867 mg, 1.96 mmol), hydroxylamine hydrochloride (649 mg, 9.27 mmol), and triethylamine (2.1 mL) to give (1S,2R)-N-hydroxy-1-(hydroxymethyl) -2-[methyl({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxamide (86.7 mg, 41%) as a colorless solid after purification via HPLC, eluting with a gradient of 15-100% MeCN/H2O (10 min). LCMS (M−H): 1.57 min, 484.3; 1H NMR (400 MHz, MeOD) δ ppm 1.44-1.49 (m, 1H) 1.56-1.62 (m, 2H) 1.64-1.68 (m, 1H) 2.02-2.12 (m, 1H) 2.67 (s, 3H) 3.43-3.53 (m, 2H) 3.67 (d, J=11.37 Hz, 1H) 5.58 (s, 2H) 7.21 (d, J=9.09 Hz, 2H) 7.50 (s, 1H) 7.56 (t, J=7.71 Hz, 1H) 7.69-7.75 (m, 1H) 7.84 (d, J=8.84 Hz, 2H) 7.96 (d, J=8.59 Hz, 1H) 8.01 (d, J=8.34 Hz, 1H).

Provenance & Evidence