Reaktion #5747

ord-9c4c8e8f7f234b989171bc299cf5fb6f

Reaktionsgleichung

CC(=O)OC(C)=O
Ac2O
CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(N)c1
(-)-2,6-dimethyl-3-carboethoxy-5-carbomethoxy-4-(3-aminophenyl)-1,4-dihydropyridine
→
CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(NC(C)=O)c1
2,6-dimethyl-3-carboethoxy-5-carbomethoxy-4-(3-acetylaminophenyl)-1,4-dihydropyridine

Edukte

CC(=O)OC(C)=O
Ac2O
CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1c1cccc(N)c1
(-)-2,6-dimethyl-3-carboethoxy-5-carbomethoxy-4-(3-aminophenyl)-1,4-dihydropyridine

Reagenzien

Keine

Lösungsmittel

c1ccncc1
pyridine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktion90 minutes after dilution with water (ml 50), extraction
  2. 2
    Sonstigewith AcOEt (3×10 ml) and crystallization from Et2O 70/EtOH 10

Vorschrift

Under inert gas atmosphere Ac2O (43 mcl) is added to a stirred solution of (-)-2,6-dimethyl-3-carboethoxy-5-carbomethoxy-4-(3-aminophenyl)-1,4-dihydropyridine (100 mg) in pyridine (ml 1). 90 minutes after dilution with water (ml 50), extraction with AcOEt (3×10 ml) and crystallization from Et2O 70/EtOH 10, give mg 85 of +)-2,6-dimethyl-3-carboethoxy-5-carbomethoxy-4-(3-acetylaminophenyl)-1,4-dihydropyridine m.p. 197°-199° C. [α]D =+0.87°, [α]578 =+2.00°, [α]546 =+1.64° c=2.2 DMF.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05245039uspto-grants-1993_09