Reaktion #67483

Reaktionsgleichung

3-nitrophthalonitrile

3-nitrophthalonitrile

K2CO3

N-Boc-serinol

→

Boc-serinol Bisphthalonitrile

Ausbeute 70.0%

Lösungsmittel

DMSO

CH3CN

benzene

CH3CN

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction mixture was partitioned between EtOAc and water
2. 2
   SonstigeThe two layers were separated
3. 3
   Extraktionthe aqueous layer was extracted 3 times with 50 mL EtOAc
4. 4
   SonstigeThe organic layer from the original partitioning
5. 5
   workup.ADDITIONwas added to the organic extract
6. 6
   WaschenThis mixture was then washed twice with 50 mL of saturated NaHCO3
7. 7
   Trocknentwice with 50 mL of water, and was then dried over Na2SO4
8. 8
   SonstigeThe solvent was removed at reduced pressure
9. 9
   Sonstigethe resulting crude orange solid was recrystallized from methanol/water
10. 10
    Sonstigeto give 2.43 g (70% yield) of a slightly pink/tan solid

Vorschrift

Finely ground K2CO3 (4.32 g, 31.2 mmol, 4 equiv.) was added to N-Boc-serinol (1.45 g, 7.8 mmol, 1 equiv.) in 20 mL DMSO under argon; then 3-nitrophthalonitrile (3.38 g, 19.5 mmol, 2.5 equiv.) was added. The reaction mixture first turned pink, and then orange upon addition of the 3-nitrophthalonitrile. The reaction mixture was stirred at room temperature and monitored periodically by TLC (9:1 benzene:CH3CN). After 72 h, the reaction mixture was partitioned between EtOAc and water. The two layers were separated, and the aqueous layer was extracted 3 times with 50 mL EtOAc. The organic layer from the original partitioning was added to the organic extract. This mixture was then washed twice with 50 mL of saturated NaHCO3, and twice with 50 mL of water, and was then dried over Na2SO4. The solvent was removed at reduced pressure, and the resulting crude orange solid was recrystallized from methanol/water to give 2.43 g (70% yield) of a slightly pink/tan solid. [Rf: 0.25 (9:1 benzene:CH3CN); melting point 167-169° C.; 1H NMR (200 MHz, CD3CN) δ 7.85-7.4 (m, 6H, ArH), 5.76 (br s, 1H, NH), 4.39 (s, 5H, (—CH2)2CH—), 1.42 (s, 9H, C(CH3)3).]

Quelle