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

HRID 551993Notes

Reaction equation

HRID 551993 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([N:22]([CH2:29][C:30]3[CH:31]=[CH:32][C:33]([F:40])=[C:34]([CH:39]=3)[C:35]([O:37]C)=[O:36])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(=[O:21])=[O:20])=[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:14]=[CH:15][C:16]([S:19]([N:22]([CH2:29][C:30]3[CH:31]=[CH:32][C:33]([F:40])=[C:34]([CH:39]=3)[C:35]([OH:37])=[O:36])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(=[O:20])=[O:21])=[CH:17][CH:18]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57554465HCID 57554465, compound

Product 1

HCID 116568635-{[({4-[(4-Butylphenyl)ethynyl]phenyl}sulfonyl)(hexyl)amino]methyl)-2-fluorobenzoic acidYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 5-{[({4-[(4-butylphenyl)ethynyl]phenyl}sulfonyl)(hexyl)amino]methyl}-2-fluorobenzoate (66 mg; 0.12 mmol) in THF (4 mL) were added lithium hydroxide monohydrate (49 mg; 1.17 mmol) and water (1 mL). The reaction mixture was stirred at 100° C. for 2500 s under MW. The mixture was poured into HCl 1N (10 mL) and extracted with EtOAc (2×75 mL). Combined organic layers were washed with brine (125 mL), dried over magnesium sulfate and filtrated. The solvent was removed under reduced pressure to give 57 mg (88.6%) of the title compound as a white powder. HPLC: Rt=5.71 min (purity=98.9%), LC/MS: M−(ESI): 548.3.1H NMR (MeOD) δ: 7.87 (d, J=8.6 Hz, 3H), 7.72 (d, J=8.6 Hz, 2H), 7.69 (m, 1H), 7.48 (d, J=7.9 Hz, 2H), 7.22 (d, J=8.2 Hz, 2H), 7.18 (s, 1H), 4.39 (s, 2H), 3.75 (m, 1H), 3.55 (t, J=4.3 Hz, 1H), 3.16 (t, J=7.3 Hz, 2H), 2.68 (t, J=7.7 Hz, 2H), 1.63 (q, J=7.5 Hz, 3H), 1.35 (m, 4H), 1.15 (m, 4H), 0.95 (t, J=7.3 Hz, 3H), 0.82 (t, J=7.0 Hz, 3H).

Workup

  1. extractionextracted with EtOAc (2×75 mL)
  2. washCombined organic layers were washed with brine (125 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-84f3ac512af049eea7f6e6035f57218b
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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