Sodium Hydroxide → {4-[4-(1-Ethoxycyclopropyl)-3-isopropyl-phenylethynyl]-phenyl]-acetic acid

HRID 1935897Notes

Reaction equation

HRID 1935897 reaction equation
[CH2:1]([O:3][C:4]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24]C)=[O:23])=[CH:17][CH:16]=3)=[CH:9][C:8]=2[CH:26]([CH3:28])[CH3:27])[CH2:6][CH2:5]1)[CH3:2].[OH-].[Na+].O.CC#N>C(O)C.O1CCCC1>[CH2:1]([O:3][C:4]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]3[CH:16]=[CH:17][C:18]([CH2:21][C:22]([OH:24])=[O:23])=[CH:19][CH:20]=3)=[CH:9][C:8]=2[CH:26]([CH3:27])[CH3:28])[CH2:6][CH2:5]1)[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 18373917Acetonitrile--water (1/1)HCID 86585929Methyl {4-[4-(1-ethoxycyclopropyl)-3-isopropyl-phenylethynyl]-phenyl}acetate2×

Product 1

HCID 22568932{4-[4-(1-Ethoxycyclopropyl)-3-isopropyl-phenylethynyl]-phenyl]-acetic acidYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Using General Procedure I; a solution of methyl {4-[4-(1-ethoxycyclopropyl)-3-isopropyl-phenylethynyl]-phenyl}-acetate (Compound 100, 130.0 mg, 0.35 mmol) in ethanol (5 mL) and tetrahydrofuran (5 mL) was treated with NaOH (120.0 mg, 3.0 mmols, 3.0 mL of a 1N aqueous solution) and stirred at 50° C. for 4 h. Work-up and isolation by HPLC (Partisil 10-pac, 10% H2O/CH3CN) afforded 88.0 mg (70%) of the title compound.

Sources & evidence

ORD record
ord-050834b12ccd4b0ab650aaae257ebaf6
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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