Methanol → HCID 16035376, compound

Participants

Reaction Conditions

Reaction Steps

N-Benzyl-N-[2-[2-(4-hydroxy-2-oxo-3H-benzothiazol-7-yl)ethylamino]ethyl]-3-phenethyloxy-propanamide (Example 4, 0.1 g) was dissolved in tetrahydrofuran (6 mL) and treated with borane (1M in tetrahydrofuran, 1 mL) at room temperature. The resultant solution was heated at 50° C. for 3 hours. The reaction was then cooled to 0° C. and methanol (6 mL) was added dropwise. Following this, the mixture was concentrated and the collected residue was dissolved in methanol (6 mL) and treated with concentrated hydrochloric acid (1.6 mL). The acidic solution was heated at 60° C. for 14 hours, then cooled to room temperature and concentrated. The resulting residue was purified by preparative HPLC (95:05, ammonia (0.2%):acetonitrile) to give the titled compound (0.035 g) as a glass like solid.

Provenance & Evidence