Triethylamine → HCID 68618081, compound

Participants

Reaction Steps

Triethylamine (0.48 mL, 3.43 mmol) followed by 3-(3-methoxy-propoxy)-4-methoxy-benzoic acid chloride (621 mg, 2.4 mmol) (prepared from 3-(3-methoxy-propoxy)-4-methoxy-benzoic acid and SOCl2 in CH2Cl2) is added to a solution of (3S*,4R*)-3-[(benzenesulfonyl-isobutyl-amino)-methyl]-4-(isopropylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.07 g, 2.3 mmol) in CH2Cl2 (30 mL) and stirred at RT for 16 h. For workup a sat. solution of NaHCO3 is added and the mixture is extracted with ethyl acetate. The combined organic extracts are dried (Na2SO4), filtered and the solvent is evaporated. Purification of the crude product by flash chromatography on silica gel (eluent gradient: c-hexane/AcOEt 1:1 to 3:7) yields the title compound. TLC, Rf (c-hexane/AcOEt 3:7)=0.40; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 6.10 min.

Provenance & Evidence