Reaktion #43811

ord-c0267d7a4d17472887b6e0ded77623d3

Reaktionsgleichung

CCCc1nc2cc(NC(=O)OC(C)(C)C)ccc2n1CC(=O)OC(C)(C)C
product
CCCc1nc2cc(NC(=O)OC(C)(C)C)ccc2n1CC(=O)OC(C)(C)C
(5-tert-Butoxycarbonylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester
[Na+].[OH-]
NaOH
→
CCCc1nc2cc(NC(=O)OC(C)(C)C)ccc2n1CC(=O)O
title compound
CCCc1nc2cc(NC(=O)OC(C)(C)C)ccc2n1CC(=O)O
(5 -tert-Butoxycarbonylamino-2-propyl-benzoimidazol-1-yl)-acetic acid

Edukte

CCCc1nc2cc(NC(=O)OC(C)(C)C)ccc2n1CC(=O)OC(C)(C)C
product
CCCc1nc2cc(NC(=O)OC(C)(C)C)ccc2n1CC(=O)OC(C)(C)C
(5-tert-Butoxycarbonylamino-2-propyl-benzoimidazol-1-yl)-acetic acid tert-butyl ester
[Na+].[OH-]
NaOH

Reagenzien

Keine

Lösungsmittel

ClCCl
DCM
CCO
ethanol

Reaktionsbedingungen

Temperatur
70°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionextracted with water
  2. 2
    Extraktionextracted with DCM
  3. 3
    WaschenThe organic layer was washed with water
  4. 4
    Einengenconcentrated
  5. 5
    Sonstigepurified by preparative LCMS

Vorschrift

The product of step d.) was dissolved in 3 mL ethanol, treated with 1 M NaOH (500 μL), and heated to 70° C. for one hour. The reaction was diluted in DCM and extracted with water. The aqueous layer was acidified with 1 M HCl and extracted with DCM. The organic layer was washed with water, concentrated and purified by preparative LCMS to give the title compound. MS: ESI (positive): 334 (M+H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07732618B2uspto-grants-2010_06