Dichloromethane → 2-(2-Isopropylsulfanyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

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Reaction Steps

A 30 mL reaction vial is charged with 2-isopropylsulfanylbenzoic acid (430 mg, 2.19 mmol) and dry DCM (7 mL). A stirring bar is added. Stirring is initiated. After dissolution is complete, the HTBU (831 mg, 2.19 mmol) is added. After 5 min, 2-amino-indane-2-carboxylic acid ethyl ester. (450 mg, 2.19 mmol) is added followed by DIPEA (0.96 mL, 5.48 mmol). The reaction is allowed to stir for 3 days. Analysis by tlc of the reaction mixture (silica, 5% iPrOH/DCM) indicates complete consumption of the starting amine. The contents of the reaction flask are transferred to a separatory funnel and diluted with EtOAc (50 mL). This is washed consecutively with dilute aqueous HCl (3%, 25 mL), saturated aqueous NaHCO3 (25 mL) and brine (25 mL), and then dried over MgSO4, filtered and evaporated in vacuo to provide 0.87 g of light yellow solid. This material is dissolved in 10 mL of DCM. This material is purified utilizing an ISCO Companion with a 40 g cartridge of silica. The gradient is 10% EtOAc in heptanes over 3 column volumes followed by a linear gradient to 50% EtOAc in heptanes over 10 column volumes. 17 mL fractions of eluent are collected. Fractions 32 through 40 are combined and evaporated in vacuo. This provides white solid material (0.69 g, 82%).

Provenance & Evidence