Ethanol → (S)-2-(Trifluoromethyl)-3-(benzylamino)propane-1,2-diol

HRID 886707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 886707
C([O:6][CH2:7][C@@:8]([OH:22])([CH2:13][NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]([F:12])([F:11])[F:10])(=O)CCC.C(O)C>Cl>[F:10][C:9]([F:11])([F:12])[C@@:8]([CH2:13][NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([OH:22])[CH2:7][OH:6]

Komponenten

4

Edukt 2

HCID 702EthanolHCID 59487502Butanoic acid (S)-2-hydroxy-2-(trifluoromethyl)-3-(benzylamino)propyl ester

Produkt 1

HCID 59487491(S)-2-(Trifluoromethyl)-3-(benzylamino)propane-1,2-diolAusbeute 104,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

(S)-3,3,3-Trifluoro-2-hydroxy-2-{[(phenylmethyl)amino]methyl}propyl butanoate (0.32 g) was dissolved in 5M hydrochloric acid (5 ml) and ethanol (5 ml) and heated at 100° C. for 3 hours. After cooling, the ethanol was evaporated and the remaining aqueous was basified with 2M sodium hydroxide and extracted with ethyl acetate (2 times). The combined organics were dried using a hydrophobic frit and evaporated to give the title compound as a pale yellow oil (0.26 g).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe ethanol was evaporated
  3. extractionextracted with ethyl acetate (2 times)
  4. customThe combined organics were dried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ca916cdd642b4f43a25789870b31a6e0
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247377B2

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