Ethanolamine → isopropyl ((2S,4R)-1-acetyl-6-(4-((2-hydroxyethyl)carbamoyl)phenyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamate

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Reaction Steps

To a solution of 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid (for a preparation see Intermediate 48) (116 mg, 0.283 mmol) and ethanolamine (0.034 mL, 0.565 mmol) in DMF (3 mL) were added HATU (161 mg, 0.424 mmol) and DIPEA (0.148 mL, 0.848 mmol). The resulting mixture was stirred at room temperature for 1 h, then water and EtOAc were added. The layers were separated and the aqueous phase was extracted with EtOAc (×3). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in 1:1 MeOH/DMSO and was purified by MDAP (formate). The appropriate fractions were combined and concentrated under reduced pressure to give isopropyl ((2S,4R)-1-acetyl-6-(4-((2-hydroxyethyl)carbamoyl)phenyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamate (102 mg, 80%) as a white solid. LCMS (Formate, 2 min), Rt=0.76 min, MH+=454.

Provenance & Evidence