Hydrochloric Acid → 5-[{4-[(4-Butylphenyl)ethynyl]benzoyl}(hexyl)amino]-2-fluorobenzoic acid

HRID 551984Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:38]=[CH:37][C:16]([C:17]([N:19]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:20]3[CH:21]=[CH:22][C:23]([F:30])=[C:24]([CH:29]=3)[C:25]([O:27]C)=[O:26])=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].O.[OH-].[Li+].O.Cl>C1COCC1>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:38]=[CH:37][C:16]([C:17]([N:19]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[C:20]3[CH:21]=[CH:22][C:23]([F:30])=[C:24]([CH:29]=3)[C:25]([OH:27])=[O:26])=[O:18])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 5-[{4-[(4-butylphenyl)ethynyl]benzoyl}(hexyl)amino]-2-fluorobenzoate (170 mg; 0.33 mmol) in THF (7 mL) were added lithium hydroxide monohydrate (139 mg; 3.31 mmol) and water (3 mL). The reaction mixture was stirred under MW at 100° C. for 2500 s. Then an aqueous solution of HCl (1N) was added and the mixture extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine, dried over magnesium sulfate and the solvent was removed under reduced pressure to give 147 mg (88.9%) of the title compound as a colorless solid. HPLC, Rt: 5.54 min (purity=98.4%), LC/MS: M−(ESI): 498.3. 1H NMR (MeOD) δ: 7.61 (m, 1H), 7.29 (d, J=7.9 Hz, 5H), 7.22 (d, J=7.9 Hz, 2H), 7.08 (d, J=7.9 Hz, 2H), 7.03 (s, 1H), 3.8 (m, 2H), 2.52 (t, J=7.5 Hz, 2H), 1.49 (q, J=7.4 Hz, 4H), 1.25 (m, 8H), 0.82 (m, 6H).

Workup

extractionthe mixture extracted with EtOAc (2×50 mL)
washThe combined organic layers were washed with brine
dry with materialdried over magnesium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-0c25f03cfcdc4c228df9c0d2dd0a7555
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947851B2

Reaction notes

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