Hydrochloric Acid → 4-({{4-[(4-Butylphenyl)ethynyl]benzyl}[2-(4-chlorophenyl)ethyl]amino}-methyl)benzoic acid

HRID 551896Notes

Reaction equation

HRID 551896 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:40]=[CH:39][C:16]([CH2:17][N:18]([CH2:28][C:29]3[CH:38]=[CH:37][C:32]([C:33]([O:35]C)=[O:34])=[CH:31][CH:30]=3)[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:40]=[CH:39][C:16]([CH2:17][N:18]([CH2:28][C:29]3[CH:38]=[CH:37][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=3)[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11519626Methyl 4-({{4-[(4-butylphenyl)ethynyl]benzyl}[2-(4-chlorophenyl)-ethyl]amino}methyl)benzoate

Product 1

HCID 115705014-({{4-[(4-Butylphenyl)ethynyl]benzyl}[2-(4-chlorophenyl)ethyl]amino}-methyl)benzoic acidYield 97.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-({{4-[(4-butylphenyl)ethynyl]benzyl}[2-(4-chlorophenyl)-ethyl]amino}methyl)benzoate (980 mg, 1.78 mmol) in MeOH (15 mL) was added an aqueous solution of NaOH (4.5 mL, 1N) and the resulting mixture was stirred at rt for 12 hrs. An aqueous solution of HCl (1N) was added and the resulting mixture was extracted with Et2O. The combined organic layers were dried over MgSO4 and evaporated to give 929 mg of 4-({{4-[(4-butylphenyl)ethynyl]benzyl}[2-(4-chlorophenyl)ethyl]amino}-methyl)benzoic acid as a colorless oil. This product was dissolved in Et2O (30 mL) and a solution of HCl in dioxane (2 mL, 4N) was added. The precipitate was filtered, washed with Et2O and dried under vacuum to give 985 mg (97%) of the title compound as a white powder. HPLC, Rt: 4.7 min (purity: 98.9%). M−(ESI): 534.3; M+(ESI): 536,2. 1H NMR (DMSO-d6) δ: 13.4 (brs, 1M), 11.3 (brs, 1H), 8.35-7.28 (m, 16H), 4.82-4.45 (m, 2H), 3.96-4.58 (m, 6H), 2.81 (t, J=7.9 Hz, 2H), 1.84-1.68 (m, 2H), 1.60-1.41 (m, 2H), 1.10 (t, J=7.2 Hz, 3H).

Workup

  1. extractionthe resulting mixture was extracted with Et2O
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-577637bb6929423b835a6c8c32303130
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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