1,2-Dichloroethane → HCID 69078832, compound

Participants

Reaction Steps

To a 250-mL round bottomed-flask equipped with a magnetic stir bar and containing a solution of N-(cyclopropylmethyl)(methylsulfonyl)(2-piperazinyl-phenyl)amine (Step 2) (1.8 g, 5.8 mmol) and (2S)-3-(4-chlorophenyl)-2-hydroxypropanoic acid (Step 1) (1.2 g, 5.8 mmol) in CH2Cl2 (30 mL) and DMF (30 mL) at RT was added HOAT (Aldrich) (0.87 g, 6.4 mmol) followed by EDC (Aldrich) (1.3 g, 7.0 mmol). This was stirred for 18 h and diluted with CH2Cl2 (300 mL). The mixture was washed with H2O (3×100 mL), aq. NaHCO3 (1×100 mL) and brine (1×100 mL). It was dried (Na2SO4) and concentrated onto silica gel. Purification by chromatography (40 to 55% EtOAc/hexanes) afforded (2S)-3-(4-chlorophenyl)-1-(4-{2-[(cyclopropylmethyl)-(methylsulfonyl)amino]-phenyl}-piperazinyl)-2-hydroxypropan-1-one as a slightly yellow oil (1.8 g). Analytically pure material was obtained by reverse phase preparative scale chromatography (Column: MetaChem Polaris C18-A 5 micron, flow: 20 mL/min, gradient: 5 to 100% CH3CN (0.1% TFA)/H2O (0.1% TFA). MS (ESI, pos. ion) m/z 492 (M+1). Calc'd for C24H30ClN3O4S: 491.16.

Provenance & Evidence