Water → 2-(7-(3-Cyano-4-isopropoxybenzyloxy)-9-(methylsulfonyl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

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Reaction Conditions

Reaction Steps

D/L-Cysteine (40.5 mg, 0.334 mmol) was dissolved in TFA (1 mL) and cooled down to 0° C. The solution was added to a solution of tert-butyl 2-(7-(3-cyano-4-isopropoxybenzyloxy)-9-(methylsulfonyl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (36 mg, 0.067 mmol) in DCM (1 mL) at 0° C. The reaction was stirred at this temperature for 1 h. Water was added, then ethyl acetate was added. The organic layer was separated, washed with water and brine, dried over anhydrous Na2SO4, and concentrated. The residue was purified by preparative HPLC. The combined fractions were partially concentrated in vacuo and diluted with ethyl acetate. The organic layer was separated, washed with water, and dried over anhydrous Na2SO4. The solvent was evaporated to give the title compound as white solid. LCMS m/z=483.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.41 (d, J=6.0 Hz, 6H), 2.46-2.55 (m, 1H), 2.84 (dd, J=16.7 and 9.5 Hz, 1H), 2.92-3.03 (m, 1H), 3.11 (s, 3H), 3.33 (dd, J=16.7, 3.4 Hz, 1H), 3.98-4.08 (m, 1H), 4.10-4.17 (m, 1H), 4.17-4.25 (m, 1H), 4.62-4.69 (m, 1H), 5.04 (s, 2H), 6.95-7.00 (m, 2H), 7.22 (d, J=8.8 Hz, 1H), 7.41 (d, J=2.4 Hz, 1H), 7.59 (dd, J=8.7, 2.2 Hz, 1H), 7.66 (d, J=2.2 Hz, 1H).

Provenance & Evidence