Tert-butyl[2-(2-cyclohexyl-ethylsulfanyl)-benzoimidazol-1-yl]-acetate → [2-(2-Cyclohexyl-ethylsulfanyl)-benzoimidazol-1-yl]-acetic acid

HRID 2389465Notes

Reaction equation

HRID 2389465 reaction equation
C([O:5][C:6](=[O:26])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17][CH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[CH:20]1([CH2:19][CH2:18][S:17][C:9]2[N:8]([CH2:7][C:6]([OH:26])=[O:5])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

3

Reactant 1

HCID 91394306Tert-butyl[2-(2-cyclohexyl-ethylsulfanyl)-benzoimidazol-1-yl]-acetate

Product 1

HCID 69316424[2-(2-Cyclohexyl-ethylsulfanyl)-benzoimidazol-1-yl]-acetic acidYield 29%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl[2-(2-cyclohexyl-ethylsulfanyl)-benzoimidazol-1-yl]-acetate (Precursor A-01b, 42 mg, 0.13 mmol) in TFA/dichloromethane (1:1, 0.5 ml) is stirred at rt for 4 h. The solvents are removed in vacuo. The crude residue is sonicated in Et2O/heptane (1:1, 1 ml) until a solid precipitates. It is rinsed with heptane and purified by flash chromatography on silica gel (AcOEt/heptane, 1:1 containing 1% of AcOH), yielding the title compound (12 mg) in 30% as a white solid: tR=6.44 min (LC-1), ESI-MS (pos.): m/z 319.12 [M+H]+, ESI-MS (neg.): m/z 317.37 [M−H]+; 1H-NMR (CDCl3): δ (ppm) 0.82-0.94 (m, 2H), 1.09-1.23 (m, 3H), 1.37 (m, 1H), 1.54 (q, 2H, SCH2CH2), 1.68 (m, 5H), 3.34 (t, 2H, SCH2), 4.88 (s, 2H, CH2CO2), 7.22 (s, 3Harom), 7.65 (m, 1Harom).

Workup

  1. customThe solvents are removed in vacuo
  2. customThe crude residue is sonicated in Et2O/heptane (1:1, 1 ml) until a solid
  3. customprecipitates
  4. washIt is rinsed with heptane
  5. custompurified by flash chromatography on silica gel (AcOEt/heptane, 1:1 containing 1% of AcOH)

Sources & evidence

ORD record
ord-46ddd73fa57b49bd84dd035b021e62ae
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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