4-(4-fluorophenyl)-7-({5-[1-hydroxy-1-(trifluoromethyl)propyl]-1,3-thiazol-2-yl}thio)-2H-chromen-2-one → HCID 178458806, Verbindung

HRID 2116638Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2116638
FC1C=CC(C2C3C(=CC([S:18][C:19]4[S:20][C:21]([C:24]([OH:31])([C:27]([F:30])([F:29])[F:28])[CH2:25][CH3:26])=[CH:22][N:23]=4)=CC=3)OC(=O)C=2)=CC=1>CCO.CCCCCC>[F:30][C:27]([F:28])([F:29])[C:24]([C:21]1[S:20][C:19]([SH:18])=[N:23][CH:22]=1)([OH:31])[CH2:25][CH3:26]

Komponenten

3

Edukt 1

HCID 112370004-(4-fluorophenyl)-7-({5-[1-hydroxy-1-(trifluoromethyl)propyl]-1,3-thiazol-2-yl}thio)-2H-chromen-2-one

Produkt 1

HCID 178458806HCID 178458806, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21879635Ethanol hexaneLösungsmittel

Versuchsvorschrift

A solution of (±)-1,1,1-trifluoro-2-(2-mercapto-1,3-thiazol-5-yl)butan-2-ol (1.2 g) from step 2 of example 1 in EtOH/hexane (20 ml, 1:4) was injected (1×1.2 g) onto a CHIRALPAK AD preparative (5 cm×50 cm) HPLC column (eluting with hexane/EtOH, 4:1; at 75 ml/min with UV detection at 280 nm). The enantiomers were separated with the faster eluting enantiomer having a retention time of ˜19 min (enantiomer #1, (2S)-1,1,1-trifluoro-2-(2-mercapto-1,3-thiazol-5-yl)butan-2-ol) and the slower eluting enantiomer having a retention time of ˜34 min (enantiomer #2, (2R)-1,1,1-trifluoro-2-2-mercapto-1,3-thiazol-5-yl)butan-2-ol). The eluants were concentrated to provide enantiomer #1 (0.468 g, 99% ee) and enantiomer #2 (0.426 g, 98% ee).

Aufarbeitung

  1. washonto a CHIRALPAK AD preparative (5 cm×50 cm) HPLC column (eluting with hexane/EtOH, 4:1; at 75 ml/min with UV detection at 280 nm)
  2. customThe enantiomers were separated with the
  3. washfaster eluting enantiomer
  4. washthe slower eluting enantiomer
  5. concentrationThe eluants were concentrated
  6. customto provide enantiomer #1 (0.468 g, 99% ee) and enantiomer #2 (0.426 g, 98% ee)

Quellen und Nachweise

ORD-Eintrag
ord-5353a990c7b7466e8b1e3c63df33fe77
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07439260B2

Notizen zur Reaktion

Wird geladen…