Hydrochloric Acid → 5-[{4-[(4-Butylphenyl)ethynyl]benzyl}(3-phenylpropyl)amino]-2-hydroxybenzoic acid, hydrochloride salt

HRID 551900Notes

Reaction equation

HRID 551900 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:42]=[CH:41][C:16]([CH2:17][N:18]([CH2:32][CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:19]3[CH:31]=[CH:30][C:22]4[O:23]C(C)(C)[O:25][C:26](=[O:27])[C:21]=4[CH:20]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].[ClH:45]>CO.C1COCC1.CO>[ClH:45].[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:42]=[CH:41][C:16]([CH2:17][N:18]([CH2:32][CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:19]3[CH:31]=[CH:30][C:22]([OH:23])=[C:21]([CH:20]=3)[C:26]([OH:27])=[O:25])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 116282596-[{4-[(4-butylphenyl)ethynyl]benzyl}(3-phenylpropyl)amino]-2,2-dimethyl-4H-1,3-benzodioxin-4-one

Product 1

HCID 1317289285-[{4-[(4-Butylphenyl)ethynyl]benzyl}(3-phenylpropyl)amino]-2-hydroxybenzoic acid, hydrochloride saltYield 32%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 6-[{4-[(4-butylphenyl)ethynyl]benzyl}(3-phenylpropyl)amino]-2,2-dimethyl-4H-1,3-benzodioxin-4-one (147 mg, 0.26 mmol) in MeOH/THF (9 ml, (2/1)) was added an aqueous solution of NaOH (0.3 mL, 5N). The reaction mixture was stirred at rt for 48 hrs. Then a solution of HCl in MeOH (2.5 mL, 1.25M) was added and the solvents were 5 removed under reduced pressure. The residue was taken up with water (5 mL), extracted with Et2O (2×5 mL) and the combined organic layers were dried over Na2SO4. The solvent was removed under reduced pressure. The residue was dissolved in a solution of HCl in Et2O (2 mL, 1N). Evaporation of the solvent gave 60 mg (32%) of the title compound as a brown foam. HPLC, Rt: 4.8 min (purity: 78.1%). LC/MS, M+(ESI): 518.4, M−(ESI): 516.3.

Workup

  1. customremoved under reduced pressure
  2. extractionextracted with Et2O (2×5 mL)
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in a solution of HCl in Et2O (2 mL, 1N)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-53f19e1a5eda4c158094e31ccb4f2165
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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