Tert-butyl [(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)oxy]acetate → [(3-{5-[2-(Methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)oxy]acetic acid

HRID 219984Notes

Reaction equation

HRID 219984 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH:28]=[CH:29][CH:30]=3)[CH2:18][O:19][CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37]>Cl.O1CCOCC1>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH:28]=[CH:29][CH:30]=3)[CH2:18][O:19][CH2:20][C:21]([OH:23])=[O:22])[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37]

Participants

4

Reactant 1

HCID 86645659Tert-butyl [(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)oxy]acetate

Product 1

HCID 59495739[(3-{5-[2-(Methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)oxy]acetic acidYield 82%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl [(3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)oxy]acetate (411 mg, 0.82 mmol) was dissolved in a 4M solution of HCl in dioxane (5 mL). The resulting mixture was stirred at RT for 5 hours. The reaction mixture was concentrated under reduced pressure to give the title compound as a colorless oil (298 mg, 82%). 1H NMR (DMSO-d6, 300 MHz): d=12.75 (brs, 1H), 8.33 (d, J=1.5 Hz, 1H), 8.18 (dd, J=7.9, 1.8 Hz, 1H), 8.13 (brs, 1H), 8.06 (m, 1H), 7.61 (m, 2H), 7.43 (d, J=8.0H, 1H), 7.37-7.26 (m, 3H), 7.15 (d, J=7.0 Hz, 1H), 4.68 (s, 2H), 4.23 (d, 2H), 4.17 (d, J=12.7 Hz, 1H), 4.17 (d, J=12.7 Hz, 1H), 4.16 (s, 2H), 3.25 (s, 3H), 2.04 (s, 3H). LC/MS (Method A): 445.3 (M+H)+. 443.4 (M−H)−. HPLC (Method A) Rt: 5.18 min (purity: 97.5%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c4837f314a0d4ba1ab6f77770b26fb1e
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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