Réaction #52497

ord-7f67946dbcda482082f2c0ad1571b93c

Équation de réaction

CCOC(=O)c1ccc(C#Cc2ccc(C3(NCc4ccccc4)CC3)cc2)cc1
ethyl 4-[4-(1-benzylamino-cyclopropyl)-phenylethynyl]-benzoate
CCOC(=O)c1ccc(C#Cc2ccc(C3(NCc4ccccc4)CC3)cc2)cc1
Compound 111
CCOC(=O)c1ccc(C#Cc2ccc(C3(NCc4ccccc4)CC3)cc2)cc1
ethyl 4-[4-(1-benzylamino-cyclopropyl)-phenylethynyl]-benzoate
[Na+].[OH-]
NaOH
→
O=C(O)c1ccc(C#Cc2ccc(C3(NCc4ccccc4)CC3)cc2)cc1
title compound
Rendement 50.1%
O=C(O)c1ccc(C#Cc2ccc(C3(NCc4ccccc4)CC3)cc2)cc1
4-[4-(1-Benzylamino-cyclopropyl)-phenylethynyl]-benzoic acid
Rendement 50.1%

Réactifs

—
aqueous solution
CCOC(=O)c1ccc(C#Cc2ccc(C3(NCc4ccccc4)CC3)cc2)cc1
ethyl 4-[4-(1-benzylamino-cyclopropyl)-phenylethynyl]-benzoate
CCOC(=O)c1ccc(C#Cc2ccc(C3(NCc4ccccc4)CC3)cc2)cc1
Compound 111
CCOC(=O)c1ccc(C#Cc2ccc(C3(NCc4ccccc4)CC3)cc2)cc1
ethyl 4-[4-(1-benzylamino-cyclopropyl)-phenylethynyl]-benzoate
[Na+].[OH-]
NaOH

Réactifs

Aucun

Solvants

CCO
ethanol
C1CCOC1
tetrahydrofuran

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

Using General Procedure I; a solution of ethyl 4-[4-(1-benzylamino-cyclopropyl)-phenylethynyl]-benzoate (Compound 111, 75.0 mg, 0.19 mmol) in ethanol (4 mL) and tetrahydrofuran (4 mL) was treated with NaOH (80.0 mg, 2.0 mmols, 2.0 mL of a 1N aqueous solution) and stirred overnight at room temperature. Work-up afforded 35.0 mg (50%) of the title compound as a colorless solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US06855512B2uspto-grants-2005_02