1,2-Dichloroethane → HCID 131725242, compound

Participants

Reaction Steps

To a 150 mL round-bottomed flask equipped with stirring was added tert-butyl 4-(2-{[(2,2-dimethoxyethyl)methylamino]carbonylamino}phenyl)-piperidinecarboxylate (Step a) (1.4 g, 3.3 mmol) and a 50% aqueous TFA soln (50 mL). The reaction mixture was stirred at RT for 2 h, then concentrated in vacuo. The residue was dissolved in CH2Cl2 (10 mL), stirred at 0° C. and treated with Boc-p-Cl-D-PheOH (Advanced ChemTech) (0.94 g, 3.15 mmol), HOBT (Novabiochem) (0.425 g, 3.15 mmol), TEA (Aldrich) (0.44 mL, 3.15 mmol) and EDC (Advanced ChemTech) (0.91 g, 4.7 mmol). The reaction was warmed to RT over 2 h and stirred at RT for 12 h. The reaction mixture was diluted with CH2Cl2 (60 mL) and the organic phase was washed with satd NaHCO3 (50 mL), and satd NaCl (50 mL), dried over Na2SO4, and concentrated in vacuo. Purification by silica gel chromatography (100% EtOAc) provided the title compound as a pale yellow oil (0.55 g). MS (ESI, pos. ion) m/z: 539 (M+1). Calc'd for C29H35ClN4O4: 538.23.

Provenance & Evidence