Reacción #1785953

ord-174104e21bf942eca47009a7ca55e65e

Ecuación de reacción

CC(C)(C)C(=O)CN1C(=O)[C@H](NC(=O)Nc2cccc(C(C)(C)C(=O)O)c2)CN(C2CCCCC2)c2ccccc21
(R)-(−)-2-[3-[3-(1-tert-Butylcarbonylmethyl-2-oxo-5-c yclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)urei do]phenyl]-2-methylpropionic acid
N[C@H]1CC[C@H](O)CC1
Trans-4-amino-cyclohexanol
→
CC(C)(C)C(=O)CN1C(=O)[C@H](NC(=O)Nc2cccc(C(C)(C)C(=O)O)c2)CN(C2CCCCC2)c2ccccc21.N[C@H]1CC[C@H](O)CC1
title compound
Rendimiento 82.8%
CC(C)(C)C(=O)CN1C(=O)[C@H](NC(=O)Nc2cccc(C(C)(C)C(=O)O)c2)CN(C2CCCCC2)c2ccccc21.N[C@H]1CC[C@H](O)CC1
(R)-2-[3-[3-(1-tert-butylcarbonylmethyl-2-oxo-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodi azepin-3-yl)ureido]phenyl]-2-methylpropionic acid trans-4-aminocyclohexanol salt
Rendimiento 82.8%

Reactantes

CC(C)(C)C(=O)CN1C(=O)[C@H](NC(=O)Nc2cccc(C(C)(C)C(=O)O)c2)CN(C2CCCCC2)c2ccccc21
(R)-(−)-2-[3-[3-(1-tert-Butylcarbonylmethyl-2-oxo-5-c yclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)urei do]phenyl]-2-methylpropionic acid
N[C@H]1CC[C@H](O)CC1
Trans-4-amino-cyclohexanol

Reactivos

Ninguno

Disolventes

CC#N
acetonitrile

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.DISSOLUTIONdissolved
  2. 2
    Temperaturaunder heat
  3. 3
    Otrocrystals so precipitated
  4. 4
    Filtraciónwere collected by filtration
  5. 5
    Otrodried

Procedimiento

(R)-(−)-2-[3-[3-(1-tert-Butylcarbonylmethyl-2-oxo-5-c yclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)urei do]phenyl]-2-methylpropionic acid (42 mg) was dissolved in acetonitrile (0.5 mL). Trans-4-amino-cyclohexanol (8 mg) was added and then dissolved under heat. After the mixture was allowed to stand overnight, crystals so precipitated were collected by filtration and dried, whereby the title compound (39 mg) was obtained. Yield: 77%.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06344452B1uspto-grants-2002_02