Trifluoroacetic acid → [5-(Benzyl-cyclopentanecarbonyl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid

HRID 15585Notes

Reaction equation

HRID 15585 reaction equation
C([O:5][C:6](=[O:35])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N:17]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:18]([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:32][CH2:33][CH3:34])(C)(C)C.C(O)(C(F)(F)F)=O>>[CH2:25]([N:17]([C:18]([CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1)=[O:19])[C:15]1[CH:14]=[CH:13][C:12]2[N:8]([CH2:7][C:6]([OH:35])=[O:5])[C:9]([CH2:32][CH2:33][CH3:34])=[N:10][C:11]=2[CH:16]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67200357[5-(Benzyl-cyclopentanecarbonyl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester

Product 1

HCID 59342511[5-(Benzyl-cyclopentanecarbonyl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid

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.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-d9d8ac986e9546658a68a37548f0e821
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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