Reaktion #1808005

ord-ee59be87594047a8a39b22ff45b47ecf

Reaktionsgleichung

CCCCCCCCCCCCCCCC(=O)OCC(CSCCC(=O)NCc1ccc(C(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1)OC(=O)CCCCCCCCCCCCCCC
4-[6,7-bis(palmitoyloxy)-4-thiaheptanoylaminomethyl]benzoyl-glutamic acid di-t-butyl ester
O=C(O)C(F)(F)F
trifiuoroacetic acid
→
CCCCCCCCCCCCCCCC(=O)OCC(CSCCC(=O)NCc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)OC(=O)CCCCCCCCCCCCCCC
title compound
Ausbeute 80.0%
CCCCCCCCCCCCCCCC(=O)OCC(CSCCC(=O)NCc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1)OC(=O)CCCCCCCCCCCCCCC
4 -[6,7,bis(palmitoyloxy)-4-thiaheptanoylaminomethyl]benzoylglutamic acid
Ausbeute 80.0%

Edukte

CCCCCCCCCCCCCCCC(=O)OCC(CSCCC(=O)NCc1ccc(C(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1)OC(=O)CCCCCCCCCCCCCCC
4-[6,7-bis(palmitoyloxy)-4-thiaheptanoylaminomethyl]benzoyl-glutamic acid di-t-butyl ester
—
Example 39
O=C(O)C(F)(F)F
trifiuoroacetic acid

Reagenzien

Keine

Lösungsmittel

ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenAfter solvent concentration under reduced pressure
  2. 2
    Sonstigethe resulting residue was crystallized from methanol-water

Vorschrift

A solution of 4-[6,7-bis(palmitoyloxy)-4-thiaheptanoylaminomethyl]benzoyl-glutamic acid di-t-butyl ester as obtained in Example 39 (325 mg) in dichloromethane (0.5 ml)-trifiuoroacetic acid (1 ml) was stirred at room temperature for 30 minutes. After solvent concentration under reduced pressure, the resulting residue was crystallized from methanol-water to yield the title compound (231 mg, yield 80%) as a colorless powder.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05506267uspto-grants-1996_04