Sodium Hydroxide → [4-(5-Imidazol-1-yl-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-ethynyl)-phenyl]-acetic acid

HRID 841511Notes

Reaction equation

HRID 841511 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[CH:21][C:20]3[CH:19]([N:23]4[CH:27]=[CH:26][N:25]=[CH:24]4)[CH2:18][CH2:17][C:16]([CH3:29])([CH3:28])[C:15]=3[CH:14]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>C(O)C>[N:23]1([CH:19]2[CH2:18][CH2:17][C:16]([CH3:29])([CH3:28])[C:15]3[CH:14]=[C:13]([C:12]#[C:11][C:8]4[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:30])=[O:2])=[CH:10][CH:9]=4)[CH:22]=[CH:21][C:20]2=3)[CH:27]=[CH:26][N:25]=[CH:24]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86585938Methyl [4-(5-imidazol-1-yl-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetate2×

Product 1

HCID 10178078[4-(5-Imidazol-1-yl-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-ethynyl)-phenyl]-acetic acidYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using General Procedure I; a solution of methyl[4-(5-imidazol-1-yl-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-ethynyl)-phenyl]-acetate (Compound 136, 50.0 mg, 0.13 mmol) in ethanol (4 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 afforded 40.0 mg (83%) of the title compound as a pale-orange solid.

Sources & evidence

ORD record
ord-5b89179190c844e1a05fb9e80219515d
Source dataset
uspto-grants-2002_04
Patent number
US06369225B1

Reaction notes

Loading…