Hydrochloric Acid → 6-chloro-4'-[5-chloro-2-(1-methanesulfonylaminocarbonyl-1-propyl-butoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

A solution of racemic (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(1-hydroxycarbonyl-1-propyl-butoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (80 mg, 0.13 mmol) and CDI (40 mg, 0.25 mmol) in DMF (2 mL) was heated at 60° C. for 2 h. Then to this solution was added a mixture of methanesulfonamide (123 mg, 1.3 mmol) and NaH (52 mg, 60%, 1.3 mmol) in DMF (2 mL), which had been stirred at room temperature for 2 h. After the resulting mixture was stirred at room temperature for 1 h, it was poured into water and the aqueous solution was acidified by concentrated HCl solution. After the aqueous phase was extracted with EtOAc twice, the combined organic layers were dried over anhydrous Na2SO4, concentrated and the residue was purified by flash column to give the title compound as a white solid (60 mg).

1. additionThen to this solution was added
2. stirringAfter the resulting mixture was stirred at room temperature for 1 h
3. extractionAfter the aqueous phase was extracted with EtOAc twice
4. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
5. concentrationconcentrated
6. customthe residue was purified by flash column

ORD record

ord-fcab63dc82c24d6e8cf8a6e952e85573

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07776875B2