Triethylamine hydrochloride → HCID 86607921, compound
Reaction equation
[OH:1][CH2:2][C@:3]1([C:32]([O:34]C)=[O:33])[CH2:7][CH2:6][CH2:5][C@H:4]1[N:8]([CH3:31])[S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[C:22]([CH3:30])[CH:21]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10].[OH-].[Na+].Cl.[CH2:39](N(CC)CC)C>>[CH3:39][C@@:4]1([N:8]([CH3:31])[S:9]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[N:23]=[C:22]([CH3:30])[CH:21]=3)=[CH:16][CH:17]=2)(=[O:11])=[O:10])[CH2:5][CH2:6][CH2:7][C@:3]1([CH2:2][OH:1])[C:32]([OH:34])=[O:33]Participants
Procedure
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).
Sources & evidence
- ORD record
- ord-b9c1c1f6350f477b80bb7ba492849094
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07595327B2
Reaction notes
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