Hydrochloric Acid → (2S)-3-methyl-2-(4-(5-(2'-methyl-2-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazol-3-yl)phenethylamino)butanoic acid

HRID 572596Notes

Reaction equation

[CH3:1][CH:2]([CH3:42])[C@H:3]([NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[CH3:37])=[C:27]([C:38]([F:41])([F:40])[F:39])[CH:26]=3)[O:22][N:21]=2)=[CH:16][CH:15]=1)[C:4]([O:6]C(C)(C)C)=[O:5].Cl>O1CCOCC1>[CH3:1][CH:2]([CH3:42])[C@H:3]([NH:11][CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:24]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[CH3:37])=[C:27]([C:38]([F:40])([F:39])[F:41])[CH:26]=3)[O:22][N:21]=2)=[CH:18][CH:19]=1)[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 70 °C

Procedure

To (2S)-tert-butyl 3-methyl-2-(4-(5-(2′-methyl-2-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazol-3-yl)phenethylamino)butanoate (86 mg; 0.15 mmol) was added 4M HCl in dioxan and the mixture was heated in a tube at 70° C. for 3 hours. The solvent was then removed in vacuo and the residue was purified by preparative HPLC to give the title compound as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 8.56 (1H, s), 8.50 (1H, d, J=8.1 Hz), 8.08 (2H, d, J=7.8 Hz), 7.65 (1H, d, J=8.1 Hz), 7.51 (2H, d, J=8.0 Hz), 7.40-7.38 (2H, m), 7.31 (1H, td, J=7.0, 2.3 Hz), 7.18 (1H, d, J=7.6 Hz), 3.09-2.80 (5H, m), 2.16 (3H, s), 1.99-1.90 (1H, m), 0.96 (6H, dd, J=6.8, 2.1 Hz). LC/MS (Method B): 524 (M+H)+. HPLC (Method H) Rt 9.20 min (Purity: 97.7%).

Workup

customThe solvent was then removed in vacuo
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-0f37095dc3b3425ea18733ef9cfc6066
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029405B2

Reaction notes

Loading…