Sodium Hydroxide → {4-[4-(1-Isopropoxycyclopropyl)-3-ethyl-phenylethynyl]-phenyl}-acetic acid

HRID 841678Notes

Reaction equation

HRID 841678 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][CH:23]([CH3:25])[CH3:24])[CH2:21][CH2:20]3)=[C:15]([CH2:26][CH3:27])[CH:14]=2)=[CH:7][CH:6]=1.[OH-].[Na+].O.CC#N>C(O)C.O1CCCC1>[CH:23]([O:22][C:19]1([C:16]2[CH:17]=[CH:18][C:13]([C:12]#[C:11][C:8]3[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:28])=[O:2])=[CH:6][CH:7]=3)=[CH:14][C:15]=2[CH2:26][CH3:27])[CH2:21][CH2:20]1)([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 18373917Acetonitrile--water (1/1)HCID 86585928Methyl{4-[4-(1-isopropoxycyclopropyl)-3-ethyl-phenylethynyl]-phenyl}-acetate2×

Product 1

HCID 10292133{4-[4-(1-Isopropoxycyclopropyl)-3-ethyl-phenylethynyl]-phenyl}-acetic acidYield 57.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using General Procedure I; a solution of methyl{4-[4-(1-isopropoxycyclopropyl)-3-ethyl-phenylethynyl]-phenyl}-acetate (Compound 96, 156.0 mg, 0.41 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with NaOH (120.0 mg, 3.0 mmols, 3.0 mL of a 1N aqueous solution) and stirred overnight at room temperature. Work-up and isolation by HPLC (partisil 10-pac, 10% H2O/CH3CN) afforded 85.0 mg (57%) of the title compound.

Sources & evidence

ORD record
ord-d1dd3b8cf39b44bdbc2807a50192d041
Source dataset
uspto-grants-2002_04
Patent number
US06369261B1

Reaction notes

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