Reaktion #9651

Reaktionsgleichung

methyl 4-[3′-fluoro-4′-(formylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate

HCl

→

methyl 4-(4′-amino-3′-fluoro-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate

Ausbeute 89.4%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was then concentrated
2. 2
   workup.ADDITIONdiluted with water
3. 3
   workup.ADDITIONthe acidity was adjusted to pH ˜7 by slow addition of saturated aqueous sodium bicarbonate solution
4. 4
   ExtraktionThe mixture was then extracted with dichloromethane
5. 5
   Waschenthe combined organic layers were washed with saturated sodium chloride solution
6. 6
   Trocknendried over sodium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue was then triturated with ethyl acetate/hexane

Vorschrift

To a solution of methyl 4-[3′-fluoro-4′-(formylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate (1.21 g, 3.39 mmol) in methanol (10 mL) was added conc. HCl (3.5 mL), and the resulting solution was stirred at rt for 16 h. The mixture was then concentrated, diluted with water, and the acidity was adjusted to pH ˜7 by slow addition of saturated aqueous sodium bicarbonate solution. The mixture was then extracted with dichloromethane, and the combined organic layers were washed with saturated sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was then triturated with ethyl acetate/hexane to afford methyl 4-(4′-amino-3′-fluoro-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate (998 mg, 89%). LC-MS ret. time 3.11 min, m/z 329.9 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.31 (s, 6H), 3.28 (s, 2H), 3.66 (s, 3H), 6.84 (t, 1H), 7.21–7.35 (m, 2H), 7.55 (d, 2H), 7.93 (d, 2H).

Quelle