tert-Butyl {2-[4-(methyl-phenyl-carbamoyl)-butylsulfanyl]-benzoimidazol-1-yl}-acetate → {2-[4-(Methyl-phenyl-carbamoyl)-butylsulfanyl]-benzoimidazol-1-yl}-acetic acid

HRID 2389474Notes

Reaction equation

HRID 2389474 reaction equation
[CH3:1][N:2]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:3]([CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[N:14]([CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=2[N:11]=1)=[O:4]>C(O)(C(F)(F)F)=O.ClCCl>[CH3:1][N:2]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:3]([CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[N:14]([CH2:15][C:16]([OH:18])=[O:17])[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=2[N:11]=1)=[O:4]

Participants

3

Reactant 1

HCID 86620025tert-Butyl {2-[4-(methyl-phenyl-carbamoyl)-butylsulfanyl]-benzoimidazol-1-yl}-acetate

Product 1

HCID 69314476{2-[4-(Methyl-phenyl-carbamoyl)-butylsulfanyl]-benzoimidazol-1-yl}-acetic acidYield 81.3%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-Butyl {2-[4-(methyl-phenyl-carbamoyl)-butylsulfanyl]-benzoimidazol-1-yl}-acetate (Precursor F-01b, 25.6 mg, 0.06 mmol) is dissolved in TFA/dichloromethane (1:1, 3 ml) and stirred for 3 h at rt. Evaporation of the solvent in vacuo and drying under high vacuum yields the title compound (19.4 mg) in 87% as a yellow oil: tR=5.20 min (LC-1), ESI-MS (pos.): m/z 398.20 [M+H]+, ESI-MS (neg.): m/z 396.19 [M−H]+; 1H-NMR (DMSO-d6): δ (ppm) 1.56 (m, 4H, CH2CH2), 2.05 (m, 2H, CH2C═O), 3.14 (s, 3H, NMe), 3.22 (m, 2H, SCH2), 5.00 (s, 2H, CH2CO2), 7.18-7.32 (m, 5Harom), 7.38 (m, 2Harom), 7.53 (m, 2Harom).

Workup

  1. customEvaporation of the solvent in vacuo
  2. customdrying under high vacuum

Sources & evidence

ORD record
ord-1c9d3f2faead4020add1d656817b6a20
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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