Trifluoroacetic acid → 5-{4-[2(R)-Aminopropoxy]benzyl}thiazolidine-2,4-dione trifluoroacetate

HRID 1682767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1682767
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([NH:15][C@H:16]([CH3:52])[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>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:15][C@H:16]([CH3:52])[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

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 228549855-{4-[2(R)-t-butoxycarbonylaminopropoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dione

Produkt 1

HCID 228549835-{4-[2(R)-Aminopropoxy]benzyl}thiazolidine-2,4-dione trifluoroacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

500 ml of trifluoroacetic acid were added dropwise, whilst ice-cooling, to a solution of 85.5 g of 5-{4-[2(R)-t-butoxycarbonylaminopropoxy]benzyl}-3-triphenylmethylthiazolidine-2,4-dione [prepared as described in step (e) above] in 700 ml of methylene chloride, and the resulting mixture was stirred at room temperature for 4 hours. At the end of this time, the reaction mixture was freed from the methylene chloride solvent and the trifluoroacetic acid by distillation under reduced pressure, and a mixture of benzene and a small amount of ethyl acetate was added to the residue. The crystals which precipitated were collected by filtration and were recrystallized from a mixture of methanol and ethyl acetate, to give the title compound as crystals, melting at 162°166° C. [α]D23 -13.0° (c=0.885, methanol)

Aufarbeitung

  1. distillationthe trifluoroacetic acid by distillation under reduced pressure
  2. additiona mixture of benzene
  3. additiona small amount of ethyl acetate was added to the residue
  4. customThe crystals which precipitated
  5. filtrationwere collected by filtration
  6. customwere recrystallized from a mixture of methanol and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4dea9982f56040879f204bf76a0a8eb2
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05635534

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