Hydrochloric Acid → N-isopropyl-N-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycine, hydrochloride salt

HRID 2410590Notes

Reaction equation

HRID 2410590 reaction equation
[CH:1]([N:4]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([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]([CH2:38][O:39][CH3:40])[CH:26]=3)[O:22][N:21]=2)[CH:15]=1)[CH2:5][C:6]([O:8]C(C)(C)C)=[O:7])([CH3:3])[CH3:2].O1CCOCC1.[ClH:47]>>[ClH:47].[CH:1]([N:4]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([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]([CH2:38][O:39][CH3:40])[CH:26]=3)[O:22][N:21]=2)[CH:15]=1)[CH2:5][C:6]([OH:8])=[O:7])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66677700tert-butyl N-isopropyl-N-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycinate

Product 1

HCID 131731800N-isopropyl-N-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycine, hydrochloride salt

Procedure

Tert-butyl N-isopropyl-N-(3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)glycinate (58 mg, 0.11 mmol) was dissolved in a 4N solution of HCl in dioxane (1.34 ml, 5.35 mmol). The reaction mixture was stirred at RT for 36 hours, and then concentrated under vacuum. The crude product was suspended in ACN and the precipitate was filtered off to give the title compound as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 9.60 (br s, 1H), 8.45 (m, 1H), 8.34 (m, 1H), 8.23-8.15 (m, 2H), 7.92-7.85 (m, 1H), 7.38 (t, J=8.0 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.40-7.26 (m, 3H), 7.18-7.12 (m, 1H), 4.46 (s, 2H); 4.23 (d, J=12.8 Hz, 1H), 4.17 (d, J=12.8 Hz, 1H), 4.18-3.85 (m, 2H), 3.81-3.58 (m, 1H), 3.26 (s, 3H), 2.04 (s, 3H), 1.34 (d, J=6.4 Hz, 6H). LC/MS (Method B): 484.3 (M−H)−, 486.3 (M+H)+. HPLC (Method A) Rt 4.67 min (Purity: 100%).

Workup

  1. concentrationconcentrated under vacuum
  2. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-9c3dfef65de440cd810478b7c7d9bfff
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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