tert-butyl N-(2-fluoro-5-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methyl-beta-alaninate → N-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methyl-beta-alanine

HRID 219978Notes

Reaction equation

HRID 219978 reaction equation
F[C:2]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]([CH2:38][O:39][CH3:40])[CH:26]=3)[O:22][N:21]=2)=[CH:16][C:3]=1[CH2:4][N:5]([CH3:15])[CH2:6][CH2:7][C:8]([O:10]C(C)(C)C)=[O:9]>Cl.O1CCOCC1>[CH3:40][O:39][CH2:38][C:27]1[CH:26]=[C:25]([C:23]2[O:22][N:21]=[C:20]([C:17]3[CH:16]=[C:3]([CH:2]=[CH:19][CH:18]=3)[CH2:4][N:5]([CH3:15])[CH2:6][CH2:7][C:8]([OH:10])=[O:9])[N:24]=2)[CH:30]=[CH:29][C:28]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37]

Participants

4

Reactant 1

HCID 67529270tert-butyl N-(2-fluoro-5-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methyl-beta-alaninate

Product 1

HCID 58066286N-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methyl-beta-alanine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-butyl N-(2-fluoro-5-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methyl-beta-alaninate obtained in step 1 was dissolved in HCl in dioxane (4M, 10 mL), stirred at RT for 30 h. After this time, solvents were removed under vacuum, residue was triturated with Et2O and filtered to give the title compound as an off-white powder. 1H NMR (DMSO-d6, 300 MHz) δ 12.74 (bs, 1H), 10.38 (bs, 1H), 8.36-8.33 (m, 1H), 8.23-8.20 (m, 1H), 8.18-8.15 (m, 1H), 7.87-7.84 (m, 1H), 7.72 (t, J=7.8 Hz, 1H), 7.44 (d, J=7.9 Hz, 1H), 7.37-7.28 (m, 3H), 7.15-7.13 (m, 1H), 4.48 (bs, 2H), 4.23 (d, J=12.7 Hz, 1H), 4.16 (d, J=12.7 Hz, 1H), 3.25 (s, 3H), 2.89-2.84 (m, 2H), 2.70 (s, 3H), 2.03 (s, 3H). LC/MS (Method B): 472.4 (M+H)+. HPLC (Method A) Rt 4.53 min (purity: 97.4%).

Workup

  1. customAfter this time, solvents were removed under vacuum, residue
  2. customwas triturated with Et2O
  3. filtrationfiltered

Sources & evidence

ORD record
ord-d60a560635964a3b8c9147bb712a987f
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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