Water → 6-chloro-4'-{5-chloro-2-[1-ethyl-1-((S)-2,3-dihydroxy-propylcarbamoyl)-propoxy]-phenyl}-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Participants

Reaction Steps

At room temperature, a mixture of racemic (2′S,3S,4′R)-6-chloro-4′-[1-ethyl-5-chloro-2-(1-hydroxycarbonyl-propoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (50 mg, 0.084 mmol), (S)-3-amino-1,2-propanediol (27 mg, 0.3 mmol), HATU (114 mg, 0.30 mmol) and DMAP (72 mg, 0.59 mmol) in DMF (2 mL) was stirred for 5 h. Then the mixture was poured into water and extracted with EtOAc thrice. The combined organic phase was washed with saturated NaCl solution twice, dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash column to give the title compound as a white solid (40 mg).

Provenance & Evidence