Réaction #43548

Équation de réaction

(R)-2-(Cyclohexylmethyl)succinic acid-1-methyl ester

diisopropylethylamine

HATU

N-(4-Fluoro-phenyl)-ethane-1,2-diamine

→

(R)-2-cyclohexylmethyl-N-[2-(4-fluoro-phenylamino)-ethyl]-succinamic acid methyl ester

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   AutreVolatiles were removed
2. 2
   Autrethe reaction
3. 3
   Autredirectly purified by automated normal-phase chromatography (0-100% ethyl acetate in hexanes gradient)

Mode opératoire

(R)-2-(Cyclohexylmethyl)succinic acid-1-methyl ester (211 mg, 0.93 mmol) from Acros Organics was treated with (500 μL, 2.87 mmol, 3.1 eq.) of diisopropylethylamine, HATU (360 mg, 1.096 mmol, 1.2 eq.) and (N-(4-Fluoro-phenyl)-ethane-1,2-diamine) (210 mg, 0.93 mmol, 1 eq.). The reagents were dissolved in dry dichloromethane (5 mL). The reaction was allowed to stir for 5 hours and monitored by LC/MS. Volatiles were removed and the reaction directly purified by automated normal-phase chromatography (0-100% ethyl acetate in hexanes gradient). (R)-2-cyclohexylmethyl-N-[2-(4-fluoro-phenylamino)-ethyl]-succinamic acid methyl ester was obtained as clear oil (220 mg, 0.60 mmol, 65%).

Source