Reaktion #77160

Reaktionsgleichung

3-amino-1-(tert-butoxycarbonylmethyl)-2-pyridinone

N-methylmorpholine

α-toluenesulfonyl chloride

→

title compound

Ausbeute 96.0%

3-Benzylsulfonylamino-1-(tert-butoxycarbonylmethyl)-2-pyridinone

Ausbeute 96.0%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe resulting solution was washed with saturated NaHCO3 (2×50 mL), 10% citric acid (3×50 mL) and brine (50 mL)
2. 2
   Trocknendried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Einengenthe filtrate was concentrated
5. 5
   Sonstigeto give a solid which
6. 6
   Waschenwas washed with ethyl acetate/hexane (1:2, 60 mL)

Vorschrift

To a solution of 3-amino-1-(tert-butoxycarbonylmethyl)-2-pyridinone (1.12 g, 5.0 mmol), and N-methylmorpholine (1.5 mL, 10.0 mmol) in methylene chloride (40 mL) was added α-toluenesulfonyl chloride (950 mg, 5.0 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h. Additional methylene chloride (50 mL) was added. The resulting solution was washed with saturated NaHCO3 (2×50 mL), 10% citric acid (3×50 mL) and brine (50 mL), and dried over Na2SO4 and filtered and the filtrate was concentrated to give a solid which was washed with ethyl acetate/hexane (1:2, 60 mL) to give the title compound as a white solid (1.8 g, 96%). 1H-NMR (300 MHz, CDCl3) δ7.42 (br s, 1H), 7.36 (d, J=7.3 Hz, 1H), 7.31 (m, 5H), 6.92 (d, J=7.0 Hz, 1H), 6.14 (t, J=7.2 Hz, 1H), 4.58 (s, 2H), 4.34 (s, 2H), 1.51 (s, 9H).

Quelle