Reacción #50865

Ecuación de reacción

di-acid

5-(3-(7-chloroquinolin-2-ylmethoxy)phenyl)-4,6-dithianonanedioic acid

triethylamine

2-chloro-1-methylpyridinium iodide

t-butylamine

→

title compound

8-t-BUTYLCARBAMYL-5-(3-(7-CHLOROQUINOLIN-2-YLMETHOXY)PHENYL)-4,6-DITHIAOCTANOIC ACID

Disolventes

CH2Cl2

CH3CN

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto afford a yellow solution
2. 2
   workup.STIRRINGThe reaction was stirred at room temperature overnight
3. 3
   OtroThe mixture was then evaporated
4. 4
   Otropartitioned between ethyl acetate and H2O
5. 5
   ExtracciónThe aqueous phase was adjusted to pH 3-4 before extraction
6. 6
   OtroThe organic phase was dried
7. 7
   Otroevaporated

Procedimiento

To a solution of di-acid (Step 2) (55 g, 0.114 mol.), triethylamine (35 mL), in CH2Cl2 (2.8 l) and CH3CN (500 mL) at 0° was added 2-chloro-1-methylpyridinium iodide (32 g, 0.126 m). The suspension was stirred 1 hr at 0° to afford a yellow solution. To this solution was added t-butylamine (14 mL). The reaction was stirred at room temperature overnight. The mixture was then evaporated, and partitioned between ethyl acetate and H2O. The aqueous phase was adjusted to pH 3-4 before extraction. The organic phase was dried and evaporated. Flash chromatography of the residue using 15% acetone and 0.2% AcOH in toluene afforded the title compound as an oil. Trituration with ethanol afforded the title compound as a white solid which was further purified by swishing in ether.

Fuente