Diisopropylcarbodiimide → HCID 67332860, compound

Participants

Reaction Steps

To a suspension of (S)-2-(4-chlorophenyl)-5-(4-(3-(ethylsulfonyl)-2-hydroxypropoxy)-3-methoxyphenyl)-4H-thieno[2,3-c]pyrrol-6(5H)-one) (46.0 mg, 0.088 mmol), DMAP (5.47 mg, 0.045 mmol) and BOC-Val-OH (22.96 mg, 0.106 mmol) in CH2Cl2 (0.401 mL) at RT was added DIC (0.022 mL, 0.141 mmol) dropwise over a period of 1 h. After stirring for an additional 2H, the reaction mixture was filtered and the filtrate was washed with cold 1N HCl (3×10 mL) and cold 10% NaHCO3 (3×10 mL) prior to drying over anhydrous Na2SO4 and concentrating under vacuum. The residue was purified by flash chromatography (silica gel, hexanes:EtOAc, 100:0 to 0:100) to afford 50.4 mg (79% yield) of the title compound as a yellow solid: HPLC retention time: 4.153 min., LCMS (ES): m/z 721 [M+H]+.

Provenance & Evidence