Réaction #1583870

ord-bfed230aeaef454cb0d11e6010ff84d6

Équation de réaction

O=S(Cl)Cl
Thionyl chloride
COC(=O)C1=C(C)NC(C)=C(C(=O)O)C1c1cccc([N+](=O)[O-])c1
5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid
COC(=O)C1=C(C)NC(C)=C(C(=O)Cl)[C@@H]1c1cccc([N+](=O)[O-])c1
methyl (R)-5-chlorocarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONAfter the completion of the dropwise addition
  2. 2
    Températureunder cooling in an ice bath until the solution
  3. 3
    AutreAfter the completion of reaction
  4. 4
    Autrethe reaction solution was rotary evaporated to dryness

Mode opératoire

Thionyl chloride (0.4 g, 3.4 mmol) was slowly added to a solution of 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (1.0 g, 3 mmol) in dichloromethane dropwisely at −25° C. After the completion of the dropwise addition, the reaction was continued under cooling in an ice bath until the solution became clear. After the completion of reaction, the reaction solution was rotary evaporated to dryness. The product was directly used in the next step.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09198902B2uspto-grants-2015_12