تفاعل #1683

ord-eff2bc0de6514ad8b023fb68fc66d9c2

معادلة التفاعل

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
المردود 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
المردود 85.0%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىthe solvents were evaporated in vacuo
  2. 2
    workup.DISSOLUTIONthe thick oily residue was dissolved in diethyl ether (1.5 L)
  3. 3
    أخرى(72 hours)
  4. 4
    ترشيحThe white precipitate was filtered
  5. 5
    غسيلwashed with diethyl ether (300 mL)
  6. 6
    أخرىdried

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05726159uspto-grants-1998_03