Ethanol → HCID 86700865, compound

HRID 881757Notes

Reaction equation

[CH2:1]([C:3]1[O:4][C:5]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]45[CH2:31][CH2:30][C:27]([CH2:32][C:33]([O:35]C)=[O:34])([CH2:28][CH2:29]4)[CH2:26][O:25]5)=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)=[O:10])=[C:6]([CH3:8])[N:7]=1)[CH3:2].O.[OH-].[Li+].O1CCCC1.C(O)C>O>[CH2:1]([C:3]1[O:4][C:5]([C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]45[CH2:29][CH2:28][C:27]([CH2:32][C:33]([OH:35])=[O:34])([CH2:30][CH2:31]4)[CH2:26][O:25]5)=[CH:20][CH:19]=3)=[CH:16][CH:17]=2)=[O:10])=[C:6]([CH3:8])[N:7]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A flask was charged with methyl 2-(1-(4′-(2-ethyl-4-methyloxazole-5-carboxamido)-[1,1′-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-4-yl)acetate (0.025 g, 0.020 mmol), lithium hydroxide monohydrate (0.030 g, 0.716 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, 10-60% acetonitrile/water, 20 minutes run, retention time ˜7 minutes) to afford (1-{4′-[(2-ethyl-4-methyl-oxazole-5-carbonyl)-amino]-biphenyl-4-yl}-2-oxa-bicyclo[2.2.2]oct-4-yl)-acetic acid (4 mg, 41%) as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.31 (t, J=7.58 Hz, 3H) 1.68-1.90 (m, 6H) 2.02-2.16 (m, 4H) 2.40 (s, 3H) 2.84 (q, J=7.58 Hz, 1H) 3.87 (s, 2H) 7.44 (d, J=8.46 Hz, 2H) 7.58 (d, J=8.59 Hz, 2H) 7.63 (d, J=8.72 Hz, 2H) 7.83 (d, J=8.72 Hz, 2H) 10.13 (s, 1H). LC/MS, [MS+] 474.22, RT: 2.65 (Condition M).

Workup

customThe mixture was purified by HPLC (0.1% NH4OH, 10-60% acetonitrile/water, 20 minutes run, retention time ˜7 minutes)

Sources & evidence

ORD record: ord-df68efb5ea6a481eb7c82de307641dbd
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993619B2

Reaction notes

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