2,3-Dihydroxybutanedioic Acid → HCID 46893929, compound

Participants

Reaction Steps

The title compound was prepared using procedures described in EXAMPLE 7, Step 5 to 8 from ethyl (3-azido-1,2,3,4-tetrahydro-9H-carbazol-9-yl)acetate (J. Med. Chem., 2005, 48, 897) and prop-2-yn-1-ylbenzene. The resulting racemic acid was resolved by HPLC using a 4.6×250 mm Chiralcel OD column eluting with 40% MeOH, 30% iPrOH, 29.75% Hexanes and 0.25% Et3N at 1 mL/min and 254 nm (retention times=8.9 and 18.3 min) to afford EXAMPLE 9.1 and 9.2 respectively. 1H NMR of EXAMPLE 9.1: 1H NMR (400 MHz, DMSO-d6): δ 12.99 (s, 1 H), 7.53 (s, 1 H), 7.39-7.29 (m, 4 H), 7.31-7.21 (m, 3 H), 7.08 (dd, 1 H), 6.99 (t, 1 H), 4.95-4.84 (m, 2 H), 4.75 (s, 1 H), 4.22 (s, 2 H), 3.20-3.08 (m, 1 H), 3.00 (dd, 1 H), 2.86 (dd, 1 H), 2.79-2.64 (m, 1 H), 2.36-2.27 (m, 1 H), 2.05-1.95 (m, 1 H). MS (+ESI) m/z: 387.1.

Provenance & Evidence