2-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid → 2-[(3-{5-[2-(Methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)oxy]ethanol
Reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].O[N:21]=[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][O:31][CH2:32][CH2:33][OH:34])[CH:25]=1)[NH2:23]>>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:12][N:23]=[C:22]([C:24]3[CH:25]=[C:26]([CH:27]=[CH:28][CH:29]=3)[CH2:30][O:31][CH2:32][CH2:33][OH:34])[N:21]=2)[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19]Participants
3
Procedure
The title compound was obtained following procedure described for example 54 step 1 but starting from Intermediate 28 (200 mg; 0.73 mmol) and Intermediate 76 (153 mg; 0.73 mmol). Purification by column chromatography (EtOAc:cHex from 10:90 to 50:50) gave the title compound as a colorless oil. 1H NMR (DMSO-d6, 300 MHz) δ 8.32 (d, J=1.5 Hz, 1H), 8.17 (dd, J=7.9, 1.8 Hz, 1H), 8.10 (bs, 1H), 8.06-8.02 (m, 1H), 7.60-7.59 (m, 1H), 7.42 (d, J=7.9 Hz, 1H), 7.36-7.26 (m, 3H), 7.15-7.13 (m, 1H), 4.69 (t, J=5.4 Hz, 1H), 4.22 (d, J=12.7 Hz, 1H), 4.16 (d, J=12.7 Hz, 1H), 3.61-3.51 (m, 4H), 3.25 (s, 3H), 2.03 (s, 3H). LC/MS (Method B): 431.3 (M+H)+. HPLC (Method A) Rt 5.50 min (Purity: 96.9%).
Workup
- customPurification by column chromatography (EtOAc:cHex from 10:90 to 50:50)
Sources & evidence
- ORD record
- ord-4866c5bc33cd4d4ca800dedd9760e596
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202865B2
Reaction notes
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