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

HRID 24192Notes

Reaction equation

HRID 24192 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3([O:22][CH2:23][CH3:24])[CH2:21][CH2:20]3)=[C:15]([CH:25]([CH3:27])[CH3:26])[CH:14]=2)=[CH:7][CH:6]=1.[OH-].[Na+].O.CC#N>C(O)C.O1CCCC1>[CH2:23]([O:22][C:19]1([C:16]2[CH:17]=[CH:18][C:13]([C:12]#[C:11][C:8]3[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:28])=[O:2])=[CH:10][CH:9]=3)=[CH:14][C:15]=2[CH:25]([CH3:26])[CH3:27])[CH2:21][CH2:20]1)[CH3:24]

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-c3cd6e7768f745d89a343d226120a257
Source dataset
uspto-grants-2005_02
Patent number
US06855512B2

Reaction notes

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