Ethanol → HCID 86700862, compound

HRID 881755Notes

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)[CH2:25][O:24]6)=[CH:19][CH:18]=4)=[CH:13][CH:12]=3)=[N:7][N:6]=2)[CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+].O1CCCC1.C(O)C>O>[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)[CH2:25][O: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

Conditions

Temperature: 50 °C

Procedure

A flask was charged with methyl 2-(1-(4′-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)-[1,1′-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-4-yl)acetate (0.040 g, 0.034 mmol), lithium hydroxide monohydrate (0.043 g, 1.040 mmol), tetrahydrofuran (1 ml), ethanol (0.3 ml) and water (0.3 ml), and stirred at 50° C. for 2 hours. The mixture was purified by HPLC (0.1% NH4OH, 10-50% acetonitrile/water, 20 minutes run, retention time ˜7 minutes) to afford {1-[4′-(5-cyclobutyl-[1,3,4]oxadiazol-2-ylamino)-biphenyl-4-yl]-2-oxa-bicyclo[2.2.2]oct-4-yl}-acetic acid (6 mg, 39%) as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.67-1.89 (m, 5H) 1.89-2.00 (m, 1H) 2.00-2.14 (m, 5H) 2.26-2.39 (m, 5H) 3.62-3.73 (m, 1H) 3.86 (s, 2H) 7.43 (d, J=8.40 Hz, 2H) 7.55 (d, J=8.50 Hz, 2H) 7.62 (s, 4H) 10.39-10.59 (br. s, 1H). LC/MS, [MS+] 459.22, RT: 2.61 (Condition M).

Workup

customThe mixture was purified by HPLC (0.1% NH4OH, 10-50% acetonitrile/water, 20 minutes run, retention time ˜7 minutes)

Sources & evidence

ORD record: ord-2d9f039517de49cd86ed035125488789
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993619B2

Reaction notes

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