Sodium Hydroxide → {4-[({[(4-Tert-butylphenyl)amino]carbonyl}{4-[(4-butylphenyl)-ethynyl]benzyl}amino)methyl]phenoxy}acetic acid

HRID 551898Notes

Reaction equation

HRID 551898 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:14]([CH2:34][C:35]2[CH:46]=[CH:45][C:38]([O:39][CH2:40][C:41]([O:43]C)=[O:42])=[CH:37][CH:36]=2)[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][CH3:33])=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([N:14]([CH2:34][C:35]2[CH:46]=[CH:45][C:38]([O:39][CH2:40][C:41]([OH:43])=[O:42])=[CH:37][CH:36]=2)[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][CH3:33])=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)=[O:13])=[CH:9][CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11541808Methyl {4-[({[(4-tert-butylphenyl)amino]carbonyl}{4-[(4-butylphenyl)-ethynyl]benzyl}amino)methyl]phenoxy}acetate

Product 1

HCID 11570731{4-[({[(4-Tert-butylphenyl)amino]carbonyl}{4-[(4-butylphenyl)-ethynyl]benzyl}amino)methyl]phenoxy}acetic acidYield 69.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl {4-[({[(4-tert-butylphenyl)amino]carbonyl}{4-[(4-butylphenyl)-ethynyl]benzyl}amino)methyl]phenoxy}acetate (70 mg, 0.11 mmol) in MeOH (1 mL) and THF (1 mL) was added an aqueous solution of NaOH (0.5 mL, 5N) and the resulting mixture was stirred at it for 3 hrs. Then the solvents were removed under reduced pressure. The residue was taken up in EtOAc and washed with an aqueous solution of HCl (1N) and brine. The organic layer was dried over MgSO4 and the solvent was removed to give 46 mg (67%) of the title compound. HPLC, Rt: 5.67 min (purity: 97.4%). 1H NMR (CD3OD) δ: 7.48 (d, J=8.3 Hz, 2H), 7.40 (d, J=7.5 Hz, 2H), 7.18-7.33 (m, 10H), 6.93 (d, J=8.7 Hz, 2H), 4.66 (s, 2H), 4.66 (s, 2H), 4.54 (s, 2H), 2.63 (t, J=7.5 Hz, 2H), 1.60 (m, 2H), 1.37 (m, 2H), 1.30 (s, 9H), 0.95 (t, J=7.2 Hz, 3H). M+(ESI): 603.4, M−(ESI): 601.3.

Workup

  1. customThen the solvents were removed under reduced pressure
  2. washwashed with an aqueous solution of HCl (1N) and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-95e5c3c844064223899c609bc434c392
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

Loading…