Methanol → HCID 178522245, compound

HRID 1713786Notes

Reaction equation

O.[OH-].[Li+].[F:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:6]=1[NH:13][C:14]1[O:18][C:17]([C:19]([NH:21][C:22]2[CH:39]=[CH:38][C:25]([O:26][C@@H:27]3[CH2:32][CH2:31][C@H:30]([C:33]([O:35]CC)=[O:34])[CH2:29][CH2:28]3)=[CH:24][CH:23]=2)=[O:20])=[N:16][N:15]=1.O.CO>C1COCC1>[F:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:6]=1[NH:13][C:14]1[O:18][C:17]([C:19]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([O:26][C@@H:27]3[CH2:28][CH2:29][C@H:30]([C:33]([OH:35])=[O:34])[CH2:31][CH2:32]3)=[CH:38][CH:39]=2)=[O:20])=[N:16][N:15]=1

Participants

Conditions

Temperature: 35 °C

Procedure

Lithium hydroxide monohydrate (184 mg, 4.38 mmol) was added in one portion to a solution of ethyl cis-4-{4-[({5-[(2,4,5-trifluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]-phenoxy}cyclohexanlecarboxylate (Example 645, 221 mg, 0.44 mmol) in a mixture of THF (4 mL), H2O (4 mL) and MeOH (8 mL) and the reaction mixture was stirred at 35° C. for 3 h. The reaction mixture was concentrated in vacuo and citric acid (40 mL) was added. The resulting mixture was filtered, washed with H2O and recrystallised from ethanol/H2O to give the title compound as a pale yellow solid (118 mg, 56%); 1H NMR δ 1.66-1.70 (4H, m), 1.75-1.83 (4H, m), 2.33-2.40 (1H, m), 4.50 (1H, s), 6.96 (2H, d), 7.67-7.74 (3H, m), 8.17 (1H, q), 10.95 (1H, s), 11.10 (1H, s), 12.05 (1H, s); MS m/e (M−H)− 475. The compound may be further recrystallised from EtOH, melting point 251-253° C.

Workup

concentrationThe reaction mixture was concentrated in vacuo and citric acid (40 mL)
additionwas added
filtrationThe resulting mixture was filtered
washwashed with H2O
customrecrystallised from ethanol/H2O

Sources & evidence

ORD record: ord-87f7ee858f944d50bf40fb641936a30d
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795283B2

Reaction notes

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