Reaction #43863

ord-d9d8ac986e9546658a68a37548f0e821

Reaction equation

CCCc1nc2cc(N(Cc3ccccc3)C(=O)C3CCCC3)ccc2n1CC(=O)OC(C)(C)C
[5 -(Benzyl-cyclopentanecarbonyl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester
O=C(O)C(F)(F)F
TFA
→
CCCc1nc2cc(N(Cc3ccccc3)C(=O)C3CCCC3)ccc2n1CC(=O)O
title compound
CCCc1nc2cc(N(Cc3ccccc3)C(=O)C3CCCC3)ccc2n1CC(=O)O
[5-(Benzyl-cyclopentanecarbonyl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid

Reactants

CCCc1nc2cc(N(Cc3ccccc3)C(=O)C3CCCC3)ccc2n1CC(=O)OC(C)(C)C
[5 -(Benzyl-cyclopentanecarbonyl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester
O=C(O)C(F)(F)F
TFA

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationconcentrated
  2. 2
    Otherpurified by preparative LCMS

Procedure

[5 -(Benzyl-cyclopentanecarbonyl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester (0.12 mmol) was treated with TFA (2 mL) for 2 hours, concentrated, and purified by preparative LCMS to give the title compound. 1H NMR (d6-DMSO) δ7.47 (d, 1H), 7.21 (m, 6H), 6.95 (m, 1H), 5.08 (s, 2H), 4.87 (s, 2H), 2.73 (t, 2H), 1.71 (m, 9H), 1.33 (m, 2H), 0.99 (t, 3H). MS calculated for C25H29N3O3+H: 420, observed: 420.

Source

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