Реакция #7415

ord-81c46fc548a2432dba9495e6a550bdcd

Уравнение реакции

C[C@@H](C(=O)N1CCC[C@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O
Benzyl (3S)-1-[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-ylcarbamate
O=C(O)C(F)(F)F
trifluoroacetic acid
→
C[C@@H](C(=O)N1CCC[C@H](N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O
title compound
Выход 93.0%
C[C@@H](C(=O)N1CCC[C@H](N)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O
N-((3S)-1-{(1S)-2-[(3S)-3-Aminopiperidin-1-yl]-1-methyl-2-oxoethyl}-2-oxopyrrolidin-3-yl )-6-chloronaphthalene-2-sulfonamide
Выход 93.0%

Реактанты

C[C@@H](C(=O)N1CCC[C@H](NC(=O)OCc2ccccc2)C1)N1CC[C@H](NS(=O)(=O)c2ccc3cc(Cl)ccc3c2)C1=O
Benzyl (3S)-1-[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-ylcarbamate
O=C(O)C(F)(F)F
trifluoroacetic acid

Реагенты

Нет

Растворители

ClCCl
DCM

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    КонцентрированиеThe mixture was concentrated under reduced pressure
  2. 2
    Другоеthe residue purified by SPE (acid ion-exchange, eluting with ethyl acetate:methanol 9:1)

Методика

Benzyl (3S)-1-[(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoyl]piperidin-3-ylcarbamate (0.128 g) was dissolved in DCM (3.5 ml) and treated with trifluoroacetic acid (10.5 ml) and stirred at room temperature for 6 h. The mixture was concentrated under reduced pressure and the residue purified by SPE (acid ion-exchange, eluting with ethyl acetate:methanol 9:1) to give the title compound (0.093 g) as a colourless oil.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07084139B2uspto-grants-2006_08