Tetrahydrofuran → HCID 66654007, compound

Participants

Reaction Steps

To a solution of (S)-1-(2-carboxymethoxy-5-chloro-phenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (165 mg, 0.36 mmol, 1.0 eq.) in DMF (0.9 mL), TBTU (138 mg, 0.43 mmol, 1.2 eq.) and DIPEA (0.19 mL, 1.08 mmol, 3.0 eq.) were added in sequence. The resulting reaction mixture was stirred at r.t. for 15 min. Then 1M hydrazine in anhydrous THF (1.99 mL, 1.99 mmol, 5.6 eq.) was added at 0° C. (exothermic). The resulting mixture was stirred at r.t. for 18 hours. The reaction mixture was diluted with DCM and then washed with sat. aq. NaHCO3 soln. The aq. phase was extracted once with DCM. The comb. org. phases were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by prep. HPLC (column: Waters XBridge, 30×75 mm, 10 um, UV/MS, basic conditions) and evaporated to give the desired product as a brown foam.

Provenance & Evidence