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

HRID 551990Notes

Reaction equation

HRID 551990 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:39]=[CH:38][C:16]([C:17]([N:19]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([F:37])=[C:31]([CH:36]=3)[C:32]([O:34]C)=[O:33])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[H-].[OH-].[Li+].O.Cl>C1COCC1>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:39]=[CH:38][C:16]([C:17]([N:19]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([F:37])=[C:31]([CH:36]=3)[C:32]([OH:34])=[O:33])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:18])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 57554527Methyl 5-{[{4-[(4-butylphenyl)ethynyl]benzoyl}(hexyl)amino]methyl}-2-fluorobenzoateHCID 86597229HCID 86597229, compound

Product 1

HCID 115058335-{[{4-[(4-Butylphenyl)ethynyl]benzoyl}(hexyl)amino]methyl}-2-fluorobenzoic acidYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 5-{[{4-[(4-butylphenyl)ethynyl]benzoyl}(hexyl)amino]methyl}-2-fluorobenzoate (350 mg; 0.66 mmol) in THF (7 mL) were added lithium hydroxide monohydride (278 mg; 6.63 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 (10 mL) was added and the mixture extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine (100 mL), dried over magnesium sulfate and the solvent was removed under reduced pressure to give 316 mg (93%) of the title compound as a colorless oil. HPLC, Rt: 5.64 min (purity=98.7%). LC/MS: M+(ESI): 514, 1H NMR (MeOD) δ: 7.88 (m, 1H), 7.50 (d, J=7.9 Hz, 2H), 7.33 (d, J=9.0 Hz, 5H), 7.1 (d, J=7.9 Hz, 3H), 4.78 (m, 1H), 4.60 (m, 1H), 2.54 (t, J=7.5 Hz, 2H), 1.51 (q, J=7.6 Hz, 5H), 1.38 (s, 3H), 1.14 (t, J=7.16 Hz, 4H), 1.02 (m, 3H).

Workup

  1. extractionthe mixture extracted with EtOAc (2×50 mL)
  2. washThe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8e5e61f07789430abe2d646570916feb
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

Loading…