ACC-9369 hydrochloride, (S)- → HCID 86756500, compound

Participants

Reaction Steps

(S)-Ethyl 3-[2-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]propionate hydrochloride (10 g, 0.029 moles) was dissolved in 6 N hydrochloric acid (200 mL). This solution was refluxed for 16 h and evaporated to dryness to give a white solid. This solid was dissolved in 50 mL of acetone with warming. Trace insoluble solid was removed by filtration through a fluted filter paper and the solution was allowed to cool to room temperature. The white crystalline solid which separated was filtered, washed with ether (2×25 mL) and air dried to give 6.2 g (0.0195 moles, 67.2%) of crude (S)-(−) 3-[2-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]propionic acid hydrochloride, m.p. 123-124° C. The crude acid (7.5 g, 0.023 moles) was dissolved in hot acetone (40 mL) and allowed to cool at room temperature. The white crystalline solid which separated was filtered, washed with ether (50 mL) and recrystallized three times as described above. The product was then dried in vacuo to give 2.5 g (0.00786 moles, 34.1%) of (S)-(−) 3-[2-[2-hydroxy-3-(isopropylamino)propoxy]phenyl]propionic acid hydrochloride as a white crystalline powder; m.p. 125.9° C., Mass spec. (MS/MS) M+1, m/z 282.42.

Provenance & Evidence