Reacción #1683

ord-eff2bc0de6514ad8b023fb68fc66d9c2

Ecuación de reacción

O=C(O)C(F)(F)F
trifluoroacetic acid
CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1
Boc-D-Phe-Pro-OBn
COc1ccccc1
anisole
N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1.O=C(O)C(F)(F)F
white powder
Rendimiento 85.0%
N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1.O=C(O)C(F)(F)F
D-Phe-Pro-OBn.TFA
Rendimiento 85.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothe solvents were evaporated in vacuo
  2. 2
    workup.DISSOLUTIONthe thick oily residue was dissolved in diethyl ether (1.5 L)
  3. 3
    Otro(72 hours)
  4. 4
    FiltraciónThe white precipitate was filtered
  5. 5
    Lavadowashed with diethyl ether (300 mL)
  6. 6
    Otrodried

Procedimiento

To a stirring solution of Boc-D-Phe-Pro-OBn (68 g, 150 mmol) in dichloromethane (50 mL) at 0° C., was added anisole (20 mL) followed by trifluoroacetic acid (400 mL). After stirring for 3 hours, the solvents were evaporated in vacuo and the thick oily residue was dissolved in diethyl ether (1.5 L) and refrigerated (72 hours). The white precipitate was filtered, washed with diethyl ether (300 mL) and dried to yield 59.4 g (85%) of white powder.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05726159uspto-grants-1998_03