Reaktion #421077

Reaktionsgleichung

(S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one

butyl 2,2-dimethylbut-3-ynoate

Et2NH

→

butyl 4-(4-((S)-1-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)-2,2-dimethylbut-3-ynoate

Ausbeute 19.0%

Lösungsmittel

Et3N

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was sparged with N2 for 10 min
2. 2
   Temperaturheated at 100 C for 2 h
3. 3
   EinengenThe mixture was concentrated
4. 4
   workup.DISSOLUTIONredissolved in EtOAc (90 mL)
5. 5
   Waschenwashed with 5% aq HCl (20 mL) and brine (20 mL)
6. 6
   Trocknendried over Na2SO4
7. 7
   SonstigeRemoval of the solvent
8. 8
   workup.WAITleft an oil (75 mg) which
9. 9
   Sonstigewas purified by prep HPLC

Vorschrift

A microwave vial was charged with (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one (50 mg, 0.12 mmol), butyl 2,2-dimethylbut-3-ynoate (40 mg, 0.23 mmol), CuI (2.2 mg, 0.012 mmol), PdCl2(PPh3)2 (5 mg, 0.008 mmol), Et3N (2 mL) and Et2NH (0.2 mL). The mixture was sparged with N2 for 10 min and heated at 100 C for 2 h. The mixture was concentrated, redissolved in EtOAc (90 mL), washed with 5% aq HCl (20 mL) and brine (20 mL), and dried over Na2SO4. Removal of the solvent left an oil (75 mg) which was purified by prep HPLC to afford butyl 4-(4-((S)-1-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)ethyl)phenyl)-2,2-dimethylbut-3-ynoate (11 mg, 19%). LC-MS Method 1 tR=2.13 min, m/z=520, 462.

Quelle