Reacción #1447083

ord-dd95b82b5e4c4811877900da96f735cf

Ecuación de reacción

C=CC(O)C(NC(=O)c1cn(C)nc1C(F)(F)F)C(=O)OCC
ethyl 3-hydroxy-2-[(1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]pent-4-enoate
CN
methylamine
C=CC(O)C(NC(=O)c1cn(C)nc1C(F)(F)F)C(=O)NC
erythro title compound
C=CC(O)C(NC(=O)c1cn(C)nc1C(F)(F)F)C(=O)NC
N-(2-Hydroxy-1-methylcarbamoylbut-3-enyl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothe solvent was removed
  2. 2
    Otrothe residue was recrystallized from acetone

Procedimiento

1.65 g (4.92 mmol) of ethyl 3-hydroxy-2-[(1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]pent-4-enoate were dissolved in methanol. At 0° C., methylamine gas was introduced for 1 h. After 16 h of stirring at RT, the solvent was removed and the residue was recrystallized from acetone. The precipitate gave 0.65 g of erythro title compound as a colorless powder, the filtrate contained 0.75 g of isomer mixture. Accordingly, the total yield was 1.40 g (89% of theory).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07879761B2uspto-grants-2011_02