Trifluoroacetic acid → {5-[(4-Fluoro-benzenesulfonyl)-(3-phenyl-propyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid

HRID 15557Notes

Reaction equation

HRID 15557 reaction equation
C([O:5][C:6](=[O:40])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N:17]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:37][CH2:38][CH3:39])(C)(C)C.C(O)(C(F)(F)F)=O>>[F:36][C:33]1[CH:34]=[CH:35][C:30]([S:27]([N:17]([CH2:18][CH2:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]2[CH:14]=[CH:13][C:12]3[N:8]([CH2:7][C:6]([OH:40])=[O:5])[C:9]([CH2:37][CH2:38][CH3:39])=[N:10][C:11]=3[CH:16]=2)(=[O:28])=[O:29])=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67201939{5-[(4-Fluoro-benzenesulfonyl)-(3-phenyl-propyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester

Product 1

HCID 11562529{5-[(4-Fluoro-benzenesulfonyl)-(3-phenyl-propyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid

Procedure

{5-[(4-Fluoro-benzenesulfonyl)-(3-phenyl-propyl)-amino]-2-propyl-benzoimidazol-1-yl}-acetic acid tert-butyl ester was treated with TFA (2 mL) for 2 hours, concentrated, and purified by preparative LCMS to give the title compound. 1H NMR (d6-DMSO) δ7.62 (m, 2H), 7.41 (m, 2H), 7.25 (m, 3H), 7.11 (d, 3H), 6.82 (m, 1H), 4.58 (s, 2H), 3.62 (t, 2H), 2.71 (t, 2H), 2.60 (m, 2H), 1.72 (m, 2H), 1.58 (m, 2H), 0.99 (t, 3H). MS calculated for C27H28FN3O4S—H: 508, observed: 508.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-40bba626c16e4f3f9ddcf65cf9f39ca8
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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