Triethylamine hydrochloride → (1S,2R)-1-ethyl-2-[methyl({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid

HRID 736828Notes

Reaction equation

[CH2:1]([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])[CH3:2].[OH-].[Na+].Cl.C(N(CC)CC)C>>[CH2:1]([C@:3]1([C:32]([OH:34])=[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:10])=[O:11])[CH3:2]

Participants

Reactant 3

HCID 11130Triethylamine hydrochloride

HCID 14798Sodium Hydroxide

HCID 86607918methyl (1S,2R)-1-ethyl-2-[methyl({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylate

Product 1

HCID 68818412(1S,2R)-1-ethyl-2-[methyl({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid

Conditions

Temperature: 100 °C

Procedure

According to the procedure of Example 56, Step 4, methyl (1S,2R)-1-ethyl-2-[methyl({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylate (147 mg, 0.296 mmol), 5M sodium hydroxide solution (0.30 mL), triethylamine hydrochloride (936.7 mg, 7 mmol) were heated in a microwave (100° C., 110 min) to provide crude (1S,2R)-1-ethyl -2-[methyl({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylic acid. To this crude residue were added BOP (677 mg, 1.53 mmol), hydroxylamine hydrochloride (634 mg, 9.06 mmol), and triethylamine (2 mL) to provide (1S,2R)-N-hydroxy-1-ethyl-2-[methyl({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxamide (79.2 mg, 0.159 mmol, 54%) as a colorless solid after purification via HPLC, eluting with a gradient of 15-100% MeCN/H20 (10 min). LCMS (M−H): 2.53 min, 496.2; 1H NMR (400 MHz, ACETONITRILE-D3) δ ppm 0.79-0.85 (m, 3H) 1.13-1.24 (m, 1H) 1.36-1.47 (m, 4H) 1.61-1.73 (m, 1H) 2.12-2.20 (m, 1H) 2.48-2.51 (m, 3H) 2.64-2.66 (m, 3H) 3.89-3.96 (m, 1H) 5.59 (d, J=1.01 Hz, 2H) 7.17-7.22 (m, 2H) 7.50 (s, 1H) 7.55 (ddd, J=8.34, 6.95, 1.14 Hz, 1H) 7.69-7.75 (m, 3H) 7.95-8.03 (m, 2H) 9.21 (s, 1H).

Sources & evidence

ORD record: ord-a405a2ca3ee248e2aa249fc7d32d0c84
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Reaction notes

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