1,2-Dichloroethane → (2r)-3-[(4-{[1h-Benzimidazol-2-yl(4-tert-butylcyclohexyl)amino]methyl}benzoyl)-amino]-2-hydroxypropanoic acid

Participants

Reaction Steps

To a solution of the title compound of Example 1 Step D (0.04 mmol, 16 mg), the hydrochloride salt of 2-hydroxy β-alanine methyl ester (0.06 mmol, 9 mg), HOBt (0.1 mmol, 15 mg), and EDC (0.12 mmol, 23 mg) in 0.4 mL of DMF was added DIEA (0.2 mmol, 35 μL). After 3 h the reaction was partitioned into EtOAc/brine. The organic phase was dried with MgSO4 and concentrated under reduced pressure. The residue was taken up in 1 mL of dioxane and a solution of LiOH (1 mmol, 24 mg) in 0.5 mL of H2O was added. The reaction was stirred at ambient temperature overnight, acidified with TFA and the product was purified by reverse-phase chromatography (Condition A) and lyophilized, affording the title compound as a white solid. MS (ESI): m/z 493 (M+H). HPLC A: 1.73 min.

Provenance & Evidence