Trifluoroacetic acid → HCID 15435851, Verbindung

HRID 1953641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1953641
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH:9]1[CH2:17][O:18][C:19]1[CH:51]=[CH:50][C:22]([CH2:23][CH:24]2[S:28][C:27](=[O:29])[N:26](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:25]2=[O:49])=[CH:21][CH:20]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>O>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH:9]1[CH2:17][O:18][C:19]1[CH:51]=[CH:50][C:22]([CH2:23][CH:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:49])=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 23298282HCID 23298282, Verbindung

Produkt 1

HCID 15435851HCID 15435851, VerbindungAusbeute 22,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3.55 g of 5-[4-(1-t-butoxycarbonylindolin-2-ylmethoxy)benzyl]-3-triphenylmethylthiazolidine-2,4-dione (prepared as described in Preparation 4) and 30 ml of trifluoroacetic acid was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was poured into water and the aqueous mixture was neutralized by the addition of sodium hydrogencarbonate, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography through silica gel, using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 0.41 g of the title compound. This product was dissolved in ethanol and precipitated by adding water, to give a powder melting at 55.8-58.2° C.

Aufarbeitung

  1. extractionafter which it was extracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customafter which the solvent was removed by distillation under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by column chromatography through silica gel
  7. additionby volume mixture of hexane and ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-c3acee23c4c345cdb1f6b9d4767ce49d
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06117893

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