Reaktion #409913

ord-40feac491c6643fe8fa44005910f6ed4

Reaktionsgleichung

COC(=O)[C@@H](N)Cc1ccccc1.Cl
L-phenylalanine methyl ester hydrochloride
O=C(O)CC1CCCC1
cyclopentylacetic acid
COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](C)N
N-(L-alaninyl)-L-phenylalanine methyl ester
C[C@H](NC(=O)OC(C)(C)C)C(=O)O
N-BOC-L-alanine
→
COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](C)NC(=O)CC1CCCC1
N-[N-(Cyclopentylacetyl)-L-alaninyl]-L-phenylalanine Methyl Ester

Edukte

COC(=O)[C@@H](N)Cc1ccccc1.Cl
L-phenylalanine methyl ester hydrochloride
O=C(O)CC1CCCC1
cyclopentylacetic acid
COC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](C)N
N-(L-alaninyl)-L-phenylalanine methyl ester
—
EtOAc hexanes
C[C@H](NC(=O)OC(C)(C)C)C(=O)O
N-BOC-L-alanine

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeprepared
  2. 2
    Sonstigefollowed by removal of the BOC-group
  3. 3
    Sonstigewas prepared as a solid (mp=137-139° C.)

Vorschrift

Following General Procedure U and using cyclopentylacetic acid (Aldrich) and N-(L-alaninyl)-L-phenylalanine methyl ester (prepared by coupling N-BOC-L-alanine (Bachem) with L-phenylalanine methyl ester hydrochloride (Bachem) using General Procedure U, followed by removal of the BOC-group using General Procedure Y), the title compound was prepared as a solid (mp=137-139° C.). The reaction was monitored by tlc (Rf=0.23 in 1:1 EtOAc/hexanes).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06211235B1uspto-grants-2001_04