Reaktion #1757221

ord-3dea320d2fa04d588423d80232581d00

Reaktionsgleichung

CC(C)C(=O)N(C1CCCCC1)[C@H]1CCN(NC(=O)[C@@H](Cc2ccc(Cl)cc2)NC2CN(C)C2C(=O)OCC2c3ccccc3-c3ccccc32)C1
(2R)-2-{Fmoc[1-(methyl)azetidine-3-yl]}amino-N-{(3S)-3-[cyclohexyl(isobutyryl)amino]pyrrolidine-1-yl}-3-(4-chlorophenyl)propionamide
→
CC(C)C(=O)N(C1CCCCC1)[C@H]1CCN(NC(=O)[C@@H](Cc2ccc(Cl)cc2)NC2CN(C)C2)C1
title compound
Ausbeute 73.5%
CC(C)C(=O)N(C1CCCCC1)[C@H]1CCN(NC(=O)[C@@H](Cc2ccc(Cl)cc2)NC2CN(C)C2)C1
(2R)-2-[1-(methyl)azetidine-3-yl]amino-N-{(3S)-3-[cyclohexyl(isobutyryl)amino]pyrrolidine-1-yl}-3-(4-chlorophenyl)propionamide
Ausbeute 73.5%

Edukte

CC(C)C(=O)N(C1CCCCC1)[C@H]1CCN(NC(=O)[C@@H](Cc2ccc(Cl)cc2)NC2CN(C)C2C(=O)OCC2c3ccccc3-c3ccccc32)C1
(2R)-2-{Fmoc[1-(methyl)azetidine-3-yl]}amino-N-{(3S)-3-[cyclohexyl(isobutyryl)amino]pyrrolidine-1-yl}-3-(4-chlorophenyl)propionamide

Reagenzien

Keine

Lösungsmittel

C1CCNCC1.CN(C)C=O
piperidine DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenthe reaction mixture was concentrated in vacuo
  2. 2
    Sonstigethe residue was purified by HPLC

Vorschrift

(2R)-2-{Fmoc[1-(methyl)azetidine-3-yl]}amino-N-{(3S)-3-[cyclohexyl(isobutyryl)amino]pyrrolidine-1-yl}-3-(4-chlorophenyl)propionamide prepared in Step D (71.1 mg, 1 mmol) was dissolved in 50% of piperidine-DMF (2 mL). After being stirred 30 min., the reaction mixture was concentrated in vacuo, and the residue was purified by HPLC to give the title compound (52 mg, 73.5%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07989634B2uspto-grants-2011_08