Reaktion #7419

ord-bce6d1b0269345ada7d58941bda39329

Reaktionsgleichung

C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)c(O[Si](c3ccccc3)(c3ccccc3)C(C)(C)C)c2)C1=O
(E)-2-(3-{[tert-butyl(diphenyl)silyl]oxy}-4-chlorophenyl)-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}ethenesulfonamide
CCCC[N+](CCCC)(CCCC)CCCC.[F-]
tetra n-butylammonium fluoride
C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)c(O)c2)C1=O
title compound
Ausbeute 83.8%
C[C@@H](C(=O)N1CCOCC1)N1CC[C@H](NS(=O)(=O)/C=C/c2ccc(Cl)c(O)c2)C1=O
(E)-2-(4-Chloro-3-hydroxyphenyl)-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}ethenesulfonamide
Ausbeute 83.8%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturto warm to room tempertaure over 3 days
  2. 2
    Einengenconcentrated under reduced pressure
  3. 3
    SonstigeThe residue was purified

Vorschrift

To a solution of (E)-2-(3-{[tert-butyl(diphenyl)silyl]oxy}-4-chlorophenyl)-N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}ethenesulfonamide (0.0078 g) in THF (0.3 ml) at −78° C. under nitrogen, tetra n-butylammonium fluoride (1M in THF, 0.014 ml) was added. The mixture was allowed to warm to room tempertaure over 3 days and then concentrated under reduced pressure. The residue was purified using mass directed preparative h.p.l.c. to give the title compound (0.0043 g) as a clear film.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07084139B2uspto-grants-2006_08