Ethyl Acetate → 5-{[4-[(4-Butylphenyl)ethynyl]benzyl}(3,3-dimethylbutyl)amino]-2-fluorobenzoic acid

HRID 551954Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:37]=[CH:36][C:16]([CH2:17][N:18]([CH2:30][CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:19]3[CH:20]=[CH:21][C:22]([F:29])=[C:23]([CH:28]=3)[C:24]([O:26]C)=[O:25])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].CCOC(C)=O>CCO>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:37]=[CH:36][C:16]([CH2:17][N:18]([CH2:30][CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:19]3[CH:20]=[CH:21][C:22]([F:29])=[C:23]([CH:28]=3)[C:24]([OH:26])=[O:25])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 65 °C

Procedure

Methyl 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(3,3-dimethylbutyl)amino]-2-fluorobenzoate (541 mg; 1.08 mmol) was dissolved in 10 mL of EtOH and sodium hydroxide (649.63 μl; 5.00 M, 3.25 mmol) was added. The reaction mixture was stirred at 65° C. for 2h30. The reaction mixture was allowed to cool down and EtOAc (50 mL) was added. The organic layer was washed three times with HCl (1M), dried over MgSO4, filtered and concentrated under reduced pressure to afford 450 mg (86%) of the title compound as a yellow solid. HPLC, Rt: 5.97 min (purity: 98.9%); LC/MS M+(ESI): 486.2, M−(ESI)=484.0; 1H NMR (CDCl3) δ: 7.44 (m, 4H), 7.32 (m, 1H), 7.20 (d, J=9.8 Hz, 2H,), 7.14 (d, J=8.3 Hz, 2H), 6.97 (m, 1H), 6.91-6.75 (m, 1H), 4.48 (s, 2H), 3.42 (m, 2H), 2.60 (t, J=7.7 Hz, 2H), 1.65-1.46 (m, 4H), 1.40-1.28 (m, 2H), 0.99-0.87 (m, 12H).

Workup

temperatureto cool down
washThe organic layer was washed three times with HCl (1M)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-be20ad64d33640c29819b06c7b7a7926
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947851B2

Reaction notes

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