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

HRID 551933Notes

Reaction equation

HRID 551933 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][CH2:32][CH2:33][CH2:34][CH3:35])[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+].Cl.O>CO>[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][CH2:32][CH2:33][CH2:34][CH3:35])[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 57554578Methyl 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2-fluorobenzoate

Product 1

HCID 116143075-[{4-[(4-Butylphenyl)ethynyl]benzyl}(hexyl)amino]-2-fluorobenzoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2-fluoro-benzoate (454 mg, 0.91 mmol) in MeOH (40 mL) was added an aqueous solution of NaOH (2.7 mL, 1N). The reaction mixture was stirred at 50° C. for 36 hrs. Then an aqueous solution of HCl (5 mL, 1N) was added and the reaction mixture was poured into water (100 mL) and extracted with Et2O (200 mL+2×100 mL). The combined organic layers were dried over MgSO4 and the solvents were removed under reduced pressure to give 396 mg (90%) of the title compound as a beige powder. HPLC, Rt: 5.8 min (purity: 99.1%). LC/MS, M+(ESI): 486.1, M−(ESI): 484.0. 1H NMR (CDCl3) δ: 7.48 (d, J=8.3 Hz, 2H), 7.44 (d, J=8.3 Hz, 2H), 7.29 (dd, J=5.6, 3.3 Hz, 1H), 7.17 (m, 4H), 6.97 (dd, J=10.2, 9.0 Hz, 1H), 6.78 (ddd, J=9.0, 3.4, 3.3 Hz, 1H), 4.52 (s, 2H), 3.39 (t, J=7.6 Hz, 2H), 2.62 (t, J=7.6 Hz, 2H), 1.61 (m, 4H), 1.42-1.25 (m, 8H), 0.94 (t, J=7.3 Hz, 3H), 0.90 (t, J=6.8 Hz, 3H).

Workup

  1. extractionextracted with Et2O (200 mL+2×100 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-46eb23b10bf64c549a301071ade72df1
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

Loading…