Diisopropylethylamine → HCID 59314331, compound

Participants

Reaction Steps

To a 40 mL vial containing a stirring bar, 2-(methylsulfinyl)benzoic acid (0.449 g, 2.44 mmol) is charged with dry DCM (7 mL). Stirring is initiated. HBTU (922 mg, 2.43 mmol) is added. The 2-aminoindane-2-carboxylic acid ethyl ester ([500 mg, 2.44 mmol) is added followed by DIPEA (0.95 mL, 8.0 mmol). The reaction is allowed to stir for 94 h. Analysis by tlc of the reaction mixture (silica, 10% MeOH/DCM) indicates complete consumption of the starting amine. The contents of the reaction flask are diluted with EtOAc (50 mL) and transferred to a separatory funnel. This is washed consecutively with dilute aqueous NaHCO3 (25 mL) and brine (25 mL), dried over MgSO4, filtered and evaporated in vacuo to provide 1.2 g of yellow foam. This material is dissolved in 10 mL of DCM and purified utilizing an ISCO Companion with a 40 g cartridge of silica. The gradient is 10% EtOAc in heptanes for 3 column volumes followed by a linear gradient to 100% EtOAc over 8 column volumes and then hold for 5 column volumes. 25 mL fractions are collected. Fractions 9 through 18 are combined and evaporated in vacuo to a constant weight to give 0.75 g of amorphous off-white solid.

Provenance & Evidence