Реакция #1869156

ord-ca9f5351d49a4a978457ad82bd1fbd60

Уравнение реакции

CCCC[C@@H](NC(=O)[C@H](N)CCCNC(=N)N)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCNC(=N)N)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)N[C@H](CCCC)C(=O)NCC(=O)N[C@H](Cc1ccc(O)cc1)C(N)=O.O=C(O)C(F)(F)F
TFA (D)Arg-(D)Nle-(D)Nle-(D)Nle-(D)Arg-(D)Nle-(D)Nle-(D)Nle-Gly-(D)Tyr-NH2
Oc1ccccc1
phenol
Cc1ccccc1
toluene
O=C(O)C(F)(F)F
TFA
CC(C)(C)OC(=O)NCC(=O)N[C@H](Cc1ccc(O)cc1)C(N)=O
Boc-Gly-(D)Tyr-NH2

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Концентрированиеconcentrated in vacuo
  2. 2
    ДругоеResidual TFA is removed by azeotropic distillation with toluene
  3. 3
    workup.ADDITIONThe residue is poured into a mixture of petroleum ether and diisopropyl ether
  4. 4
    ФильтрацияThe solid is filtered
  5. 5
    Промывкаwashed with diisopropyl ether
  6. 6
    Другоеdried in vacuo

Методика

The deprotected peptide SF1257-13 (TFA-(D)Arg-(D)Nle-(D)Nle-(D)Nle-(D)Arg-(D)Nle-(D)Nle-(D)Nle-Gly-(D)Tyr-NH2 (SEQ ID NO:1) is made by slowly adding TFA (A×3 l) to a mixture of SF1257-12 (A kg) and phenol (A×0.1 kg) in toluene and THF while maintaining the temperature at ≦18° C. The reaction mixture is allowed to warm up to room temperature. Following completion of cleavage, the solvent is diluted with THF and then concentrated in vacuo. Residual TFA is removed by azeotropic distillation with toluene. The residue is poured into a mixture of petroleum ether and diisopropyl ether. The solid is filtered, washed with diisopropyl ether and dried in vacuo.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07498309B2uspto-grants-2009_03