1-Hydroxybenzotriazole → HCID 59038461, compound

Participants

Reaction Steps

N,N-dicyclohexylcarbodiimide (5.12 g, 24.84 mmol) and 1-hydroxybenzotriazole (3.08 g, 24.84 mol) were added to a solution of 3-chloro-4-(methoxycarbonyl)benzoic acid (Example 72; 5.0 g, 23.7 mmol) and (R)-(+)-1-(naphthalen-1-yl)ethylamine (3.45 g, 20.7 mmol) in N,N-dimethylformamide (10 mL). The solution was stirred for 6 h at room temperature, then after the volatiles were removed in vacuo, the residual material was partitioned between ethyl acetate and water. The separated aqueous phase was extracted with three portions of ethyl acetate , then the combined ethyl acetate layers were washed with brine, dried (Na2SO4) and evaporated under reduced pressure. The resulting colorless solid was crystallized from dichloromethane/hexane to yield 8.85 g of (R)-2-chloro-4-[[1-(naphthalen-1-yl)ethylamino]carbonyl]benzoic acid methyl ester (over theory; material 94% pure by analytical HPLC).

Provenance & Evidence