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

HRID 15581Notes

Reaction equation

HRID 15581 reaction equation
C([O:5][C:6](=[O:33])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N:17]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:30][CH2:31][CH3:32])(C)(C)C.C(O)(C(F)(F)F)=O>>[CH2:23]([N:17]([C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[C:15]1[CH:14]=[CH:13][C:12]2[N:8]([CH2:7][C:6]([OH:33])=[O:5])[C:9]([CH2:30][CH2:31][CH3:32])=[N:10][C:11]=2[CH:16]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67200174[5-(Benzyl-isobutyryl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid tert-butyl ester

Product 1

HCID 59342522[5-(Benzyl-isobutyryl-amino)-2-propyl-benzoimidazol-1-yl]-acetic acid

Procedure

[5-(Benzyl-isobutyryl-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) δ7.55 (m, 1H), 7.25 (m, 6H), 7.03 (m, 1H), 5.14 (s, 2H), 4.88 (s, 2H), 3.20 (m, 2H), 2.80 (m, 1H), 1.72 (m, 2H), 1.25 (m, 6H), 0.95 (t, 3H). MS calculated for C23H27N3O3+H: 394, observed: 394.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-8fd8a6b1aafd428eb54a562dcd655185
Source dataset
uspto-grants-2010_06
Patent number
US07732618B2

Reaction notes

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