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

HRID 219973Notes

Reaction equation

HRID 219973 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:21]=[C:22]([CH:34]=[CH:35][CH:36]=3)[CH2:23][N:24]([CH3:33])[CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])[N:16]=2)=[CH:11][C:10]=1[CH2:37][O:38][CH3:39])[CH3:2].[ClH:40].O1CCOCC1>>[ClH:40].[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:21]=[C:22]([CH:34]=[CH:35][CH:36]=3)[CH2:23][N:24]([CH3:33])[CH2:25][C:26]([OH:28])=[O:27])[N:16]=2)=[CH:11][C:10]=1[CH2:37][O:38][CH3:39])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67528193tert-butyl N-(3-{5-[2'-ethyl-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate

Product 1

HCID 131729780N-(3-{5-[2'-ethyl-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycine, hydrochloride saltYield 78%

Procedure

To, tert-butyl N-(3-{5-[2′-ethyl-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate obtained in step 1 was added HCl 4M in dioxane (5.92 mL; 4 M; 23.69 mmol). The mixture was stirred at RT for 16 h. Solvents were concentrated to dryness to afford the title compound as a white powder (189 mg; 78%). 1H NMR (DMSO-d6, 300 MHz) δ 8.34 (t, J=1.7 Hz, 2H), 8.23 (d, J=7.6 Hz, 1H), 8.17 (dd, J=7.9, 1.8 Hz, 1H), 7.8 (d, J=7.6 Hz, 1H), 7.72 (t, J=7.5 Hz, 1H), 7.46 (d, J=7.9 Hz, 1H), 7.42-7.40 (m, 2H), 7.34-7.26 (m, 1H), 7.12 (d, J=7.3 Hz, 1H), 4.50 (s, 2H), 4.26-4.12 (m, 4H), 3.27 (s, 3H), 2.82 (s, 3H), 2.46-2.23 (m, 2H), 1 (t, J=7.5 Hz, 3H). LC/MS (Method B): 470.3 (M−H)−, 472.3 (M+H)+. HPLC (Method A) Rt 4.28 min (Purity: 98.9%). CHN analysis: [C28H29N3O4.HCl.0.04 Dioxane.0.2H20] Calculated: C, 65.66%; H, 6.01%; N, 8.16%; Cl, 6.88%. Found: C, 65.50%; H, 5.86%; N, 8.37%; Cl, 6.98%.

Workup

  1. concentrationSolvents were concentrated to dryness

Sources & evidence

ORD record
ord-ae94bc64a9794ea29abc052c1e444f87
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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