Reacción #1175725

Ecuación de reacción

1-Hydroxybenzotriazole

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

6-methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)naphthoic acid

methyl sarcosinate hydrochloride

triethylamine

→

product

Rendimiento 81.0%

N-[[6-Methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-methylglycine, Methyl Ester

Rendimiento 81.0%

Disolventes

DMF

DMF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added to the reaction
2. 2
   Extracciónextracted with ether (3×250 mL)
3. 3
   Secadodried with magnesium sulfate
4. 4
   Otrothe ether was removed
5. 5
   Otrochromatographed (13:7→1:1 petroleum ether:ethyl acetate, silica)

Procedimiento

1-Hydroxybenzotriazole (5.05 g, 1.5 eq) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (5.74 g, 1.2 eq) were added to a stirred solution of 6-methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)naphthoic acid, prepared by the process of Example 14 (9.18 g, 24.9 mmol) in anhydrous DMF (90 mL) at room temperature under a dry nitrogen atmosphere. After 11/4 hours, a suspension of methyl sarcosinate hydrochloride (6.96 g, 2.0 eq) in anhydrous DMF (40 mL) was added to the reaction followed by triethylamine (11.12 mL, 3.2 eq). After 30 minutes, the reaction was diluted with water (1.5 L) and extracted with ether (3×250 mL). The extracts were combined, dried with magnesium sulfate, and the ether was removed. The crude product was flash chromatographed (13:7→1:1 petroleum ether:ethyl acetate, silica) to provide the product as a clear oil (9.15 g, 81%). A small sample was triturated in petroleum ether to provide a white solid for analysis, m.p. 91.5°-93° C.

Fuente