Sodium Hydroxide → 2-(4-(4'-(5-Cyclobutyl-1,3,4-oxadiazol-2-ylamino)biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

HRID 881728Notes

Reaction equation

[CH:1]1([C:5]2[O:9][C:8]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][C:20]([C:23]56[CH2:30][CH2:29][C:26]([CH2:31][C:32]([O:34]C)=[O:33])([CH2:27][CH2:28]5)[O:25][CH2:24]6)=[CH:19][CH:18]=4)=[CH:13][CH:12]=3)=[N:7][N:6]=2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>>[CH:1]1([C:5]2[O:9][C:8]([NH:10][C:11]3[CH:12]=[CH:13][C:14]([C:17]4[CH:22]=[CH:21][C:20]([C:23]56[CH2:28][CH2:27][C:26]([CH2:31][C:32]([OH:34])=[O:33])([CH2:29][CH2:30]5)[O:25][CH2:24]6)=[CH:19][CH:18]=4)=[CH:15][CH:16]=3)=[N:7][N:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 86700834Methyl 2-(4-(4'-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Product 1

HCID 721884242-(4-(4'-(5-Cyclobutyl-1,3,4-oxadiazol-2-ylamino)biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

Procedure

The title compound was prepared analogous to Example 4, Step 4, starting from methyl 2-(4-(4′-(5-cyclobutyl-1,3,4-oxadiazol-2-ylamino)biphenyl-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (252 mg, 0.53 mmol) and NaOH (1.60 ml, 1.60 mmol). After acidification with 1N HCl, the slurry was filtered and washed with water to afford the title compound as white solid after drying (226 mg, 92% yield). HR/MS (M+H)+ found 460.2221. calc. 476.2236. RT: 2.68 (Condition L). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.53 (s, 1H) 7.62 (s, 4H) 7.57 (d, J=8.59 Hz, 2H) 7.38 (d, J=8.59 Hz, 2H) 3.89 (s, 2H) 3.62-3.73 (m, 1H) 2.22-2.41 (m, 6H) 1.82-2.11 (m, 10H)

Workup

customThe title compound was prepared analogous to Example 4, Step 4
filtrationAfter acidification with 1N HCl, the slurry was filtered
washwashed with water

Sources & evidence

ORD record: ord-9a76fd0e3ccf488d953fa56bb4d80794
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993619B2

Reaction notes

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