Dimethylformamide → HCID 68663362, compound

Participants

Reaction Steps

Oxopiperazine vii (0.16 g, 0.75 mmol) is combined with HOAt (0.11 g, 0.81 mmol) and HATU (0.31 g, 0.82 mmol) in 5 mL of dry DMF at 0° C. under N2. After 0.5 h a solution of diisopropylethylamine (0.39 mL, 2.2 mmol) and [3-amino-4-(3,5-difluoro-phenyl)-2-hydroxy-butyl]-(4-ethyl-benzyl)-carbamic acid benzyl ester (0.38 g, 0.81 mmol) in 5 mL anhydrous DMF is added. The solution is allowed to stir for 16 h at ambient temperature. The reaction is quenched by the addition of 1M HCl and diluted with ethyl acetate. The phases are separated and the aqueous layer is extracted with ethyl acetate. The combined organics are washed with 1M HCl, saturated aqueous NaHCO3 and dried over Na2SO4. The mixture is filtered and concentrated to give an oil which is purified by flash chromatography on a BIOTAGE 40S column eluting with 400 mL of heptane, followed by 1 L of 2/1: heptane/EtOAC and 97/3: CH2Cl2/MeOH to give H as a yellow oil (0.2 g, 0.3 mmol, 40%). (MS:M+H:665.3)

Provenance & Evidence