4-Methylmorpholine → 2-[(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino) pyrrolidin-2-yl]-N-[(2S)-2-hydroxy-2-phenylethyl] acetamide

Participants

Reaction Steps

To a solution of [(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino)pyrrolidin-2-yl]acetic acid (Intermediate 7, 25 mg, 0.07 mmol) in tetrahydrofuran (1 ml) at −25° C. were added NMM (18 mg, 0.18 mmol) followed by isobutyl chloroformate (10 mg, 0.07 mmol). The reaction mixture was stirred 10 min then a solution of (S)-2-amino-1-phenylethanol (10 mg, 0.07 mmol) in tetrahydrofuran (1 ml). The reaction was allowed to warm up to room temperature and was stirred overnight. Dichloromethane was added and the organic phase was washed with NH4Cl, NaHCO3 then brine. The organic phase was dried (MgSO4) and concentrated to afford 2-[(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxyimino) pyrrolidin-2-yl]-N-[(2S)-2-hydroxy-2-phenylethyl]acetamide (35 mg). Yield: 94%. HPLC purity: 90%

Provenance & Evidence