Reacción #158008

Ecuación de reacción

(R)-tert-butyl 4-(4-ethoxy-1-(5′-fluoro-2′-methoxybiphenyl-4-yl)-4-oxobutan-2-ylamino)-4-oxobutanoate

1,4-dioxane

→

(R)-4-(4-ethoxy-1-(5′-fluoro-2′-methoxybiphenyl-4-yl)-4-oxobutan-2-ylamino)-4-oxobutanoic acid

Rendimiento 41.0%

Disolventes

HCl

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónthe reaction mixture is concentrated under reduced pressure
2. 2
   OtroThe obtained residue is purified by RP-HPLC (SunFire C18, H2O (0.1% TFA)/CH3CN)

Procedimiento

A solution of (R)-tert-butyl 4-(4-ethoxy-1-(5′-fluoro-2′-methoxybiphenyl-4-yl)-4-oxobutan-2-ylamino)-4-oxobutanoate, (65 mg, 0.13 mmol) in 4M HCl in 1,4-dioxane (671 μL, 2.68 mmol) is stirred at room temperature. After stirring for 1 hour, the reaction mixture is concentrated under reduced pressure. The obtained residue is purified by RP-HPLC (SunFire C18, H2O (0.1% TFA)/CH3CN), and then lyophilized to give (R)-4-(4-ethoxy-1-(5′-fluoro-2′-methoxybiphenyl-4-yl)-4-oxobutan-2-ylamino)-4-oxobutanoic acid (23 mg). HPLC retention time=1.66 minutes (condition D); MS (m+1)=432.3; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.17 (t, J=7.1 Hz, 3 H) 2.21-2.32 (m, 2 H) 2.32-2.40 (m, 2 H) 2.40-2.48 (m, 2 H) 2.77 (d, J=6.8 Hz, 2 H) 3.74 (s, 3 H) 4.03 (q, J=7.1 Hz, 2 H) 4.19-4.33 (m, 1 H) 7.04-7.20 (m, 3 H) 7.23 (d, J=8.1 Hz, 2 H) 7.43 (d, J=8.1 Hz, 2 H) 7.93 (d, J=8.3 Hz, 1 H)

Fuente