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

HRID 551987Notes

Reaction equation

HRID 551987 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]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:23]3[CH:24]=[CH:25][C:26]([F:33])=[C:27]([CH:32]=3)[C:28]([O:30]C)=[O:29])(=[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:18]=[CH:17][C:16]([S:19]([N:22]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:23]3[CH:24]=[CH:25][C:26]([F:33])=[C:27]([CH:32]=3)[C:28]([OH:30])=[O:29])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57554500Methyl 5-[({4-[(4-butylphenyl)ethynyl]phenyl}sulfonyl)(hexyl)amino]-2-fluorobenzoate

Product 1

HCID 115639385-[({4-[(4-Butylphenyl)ethynyl]phenyl}sulfonyl)(hexyl)amino]-2-fluorobenzoic acidYield 91.7%

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]-2-fluorobenzoate (207 mg; 0.38 mmol) in anhydrous THF (7 mL) were added lithium hydroxide monohydrate (158 mg; 3.77 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 185 mg (91.7%) of the title compound as a brown cream. HPLC, Rt: 5.71 min (purity=98.5%). LC/MS, M−(ESI): 534.3. 1H NMR (MeOD) δ: 7.66 (d, J=8.66 Hz, 2H), 7.58 (d, J=8.66 Hz, 3H), 7.46 (d, J=7.91 Hz, 2H), 7.31. (m, 1H), 7.23 (m, 3H), 3.61 (m, 3H), 2.66 (t, J=7.53 Hz, 2H), 1.63 (qt, J=7.34 Hz, 2H), 1.35 (m, 12H), 0.96 (t, J=7.91 Hz, 3H), 0.87 (t, J=6.97 Hz, 3H).

Workup

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

Sources & evidence

ORD record
ord-10920b2582104329b40d77d160cb9712
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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