Reaktion #2021769

Reaktionsgleichung

compound ( 37 )

2-(2-amino-1-methylpropyl)-4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]-phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

(S)-phenyl oxirane

(S)-phenyl oxirane

→

compound 81

4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-[2[(2-hydroxy-2-phenylethyl)amino]-1-methylpropyl]-3H-1,2,4-triazol-3-one

Lösungsmittel

2-propanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed overnight
2. 2
   workup.STIRRINGThe mixture was stirred
3. 3
   Temperaturrefluxed for 3 hours
4. 4
   SonstigeThe solvent was evaporated
5. 5
   SonstigeThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 99/1)
6. 6
   SonstigeThe pure fractions were collected
7. 7
   Sonstigethe solvent was evaporated
8. 8
   SonstigeThe residue was triturated in DIPE
9. 9
   Filtrationfiltered off
10. 10
    Sonstigedried

Vorschrift

A mixture of compound (37) (0.0043 mol) and (S)-phenyl oxirane (0.005 mol) in 2-propanol (50 ml) was stirred and refluxed overnight. (S)-phenyl oxirane (0.005 mol) was added again. The mixture was stirred and refluxed for 3 hours. The solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 99/1). The pure fractions were collected and the solvent was evaporated. The residue was triturated in DIPE, filtered off and dried, yielding 1.6 g (47%) of [2S-[2α,4α[(S*,R*)(R*)]]]4-[4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-[2[(2-hydroxy-2-phenylethyl)amino]-1-methylpropyl]-3H-1,2,4-triazol-3-one (compound 81).

Quelle