Réaction #1683

ord-eff2bc0de6514ad8b023fb68fc66d9c2

Équation de réaction

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
Rendement 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
Rendement 85.0%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autrethe solvents were evaporated in vacuo
  2. 2
    workup.DISSOLUTIONthe thick oily residue was dissolved in diethyl ether (1.5 L)
  3. 3
    Autre(72 hours)
  4. 4
    FiltrationThe white precipitate was filtered
  5. 5
    Lavagewashed with diethyl ether (300 mL)
  6. 6
    Autredried

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05726159uspto-grants-1998_03