Reacción #42303

ord-20201984300a44be9a2d0db57120a64f

Ecuación de reacción

CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1
3-(cyanomethyl)-5-[(dipropylamino)carbonyl]benzoic acid
CCCN(CCC)C(=O)c1cc(C(N)=O)cc(C(=O)O)c1
3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoic acid
COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1.O=C(O)C(F)(F)F
(2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol
COc1cccc(CNC[C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)c1.O=C(O)C(F)(F)F
(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol trifluoroacetate
CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F
HATU
CCCN(CCC)C(=O)c1cc(CC#N)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1
title compound
CCCN(CCC)C(=O)c1cc(CC#N)cc(C(=O)N[C@@H](Cc2ccccc2)[C@H](O)CNCc2cccc(OC)c2)c1
N1-{(1S,2R)-1-benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-5-(cyanomethyl)-N3,N3-dipropylisophthalamide

Disolventes

Condiciones de reacción

Temperatura
40°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroovernight
  2. 2
    TemperaturaAfter cooling
  3. 3
    Lavadothe mixture is washed with water
  4. 4
    Otrothe organic phase is separated
  5. 5
    Secadodried over magnesium sulfate

Procedimiento

A mixture of 3-(cyanomethyl)-5-[(dipropylamino)carbonyl]benzoic acid (IX, 0.13 g), (2R,3S)-3-amino-1-[(3-methoxybenzyl)amino]-4-phenyl-2-butanol (VIII, 0.14 g), HATU (0.17 g), and dichloromethane (10 mL) is stirred at 40 degrees C. overnight. After cooling, the mixture is washed with water and the organic phase is separated and dried over magnesium sulfate and taken to dryness under reduced pressure. Chromatography (silica gel) gives the title compound, M+H=571.2

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07727997B2uspto-grants-2010_06