Trifluoroacetic acid → HCID 131727326, Verbindung

To a solution of racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(5-fluoro-2-methylphenyl)-2,3-dihydro-1′-[(tert-butoxycarbonyl)methyl]-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (0.54 g, 0.76 mmol) prepared in example 55c in dichloromethane (10 mL) was added trifluoroacetic acid (20 mL). The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated. The residue was redissolved in methanol (10 mL). To the resulting solution was added N,N′-diisopropylethylamine (1 mL, 5.53 mmol) and the crude was refluxed for 1 h. The reaction mixture was concentrated and the residue was partitioned between ethyl acetate and HCl aqueous solution (1N). The organic layer was separated, dried over MgSO4 and concentrated. The residue was triturated with ethyl acetate and hexane to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(5-fluoro-2-methylphenyl)-1′-hydroxycarbonylmethylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (Yield 0.3 g, 75%).

1. concentrationThe reaction mixture was concentrated
2. dissolutionThe residue was redissolved in methanol (10 mL)
3. temperaturethe crude was refluxed for 1 h
4. concentrationThe reaction mixture was concentrated
5. customthe residue was partitioned between ethyl acetate and HCl aqueous solution (1N)
6. customThe organic layer was separated
7. dry with materialdried over MgSO4
8. concentrationconcentrated
9. customThe residue was triturated with ethyl acetate and hexane

ORD-Eintrag

ord-904d7ca529824c43af745dc1a83920de

Quelldatensatz

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07495007B2