Reaktion #1807679

ord-ea02a28b7d764a5ba1be6732bf751c5b

Reaktionsgleichung

O=C(NCc1ccccc1)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(O)COc1ccccc1
(2S)-1-(N-Benzylaminocarbonyl-L-prolyl)-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine
C(=NC1CCCCC1)=NC1CCCCC1.CS(C)=O
DMSO DCC
→
O=C(COc1ccccc1)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)NCc1ccccc1
title compound
Ausbeute 53.8%
O=C(COc1ccccc1)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)NCc1ccccc1
(2S)-1-(N-Benzylaminocarbonyl-L-prolyl)-2-(phenoxyacetyl)-pyrrolidine
Ausbeute 53.8%

Edukte

O=C(NCc1ccccc1)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(O)COc1ccccc1
(2S)-1-(N-Benzylaminocarbonyl-L-prolyl)-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine
C(=NC1CCCCC1)=NC1CCCCC1.CS(C)=O
DMSO DCC

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigefollowed by recrystallization from ethyl acetate-hexane

Vorschrift

(2S)-1-(N-Benzylaminocarbonyl-L-prolyl)-2-(1-hydroxy-2-phenoxyethyl)pyrrolidine (798 mg) was subjected to DMSO-DCC oxidation as in Example 1D), followed by recrystallization from ethyl acetate-hexane to give 427 mg of the title compound (See Table 6).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05506256uspto-grants-1996_04