Tert-butyl[2-(5-ethyloxycarbonyl-pentylsulfanyl)-benzoimidazol-1-yl]-acetate → [2-(5-Ethyloxycarbonyl-pentylsulfanyl)-benzoimidazol-1-yl]-acetic acid

HRID 2389472Notes

Reaction equation

HRID 2389472 reaction equation
C([O:5][C:6](=[O:28])[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][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[CH2:26]([O:25][C:23]([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][S:17][C:9]1[N:8]([CH2:7][C:6]([OH:28])=[O:5])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=1)=[O:24])[CH3:27]

Participants

3

Reactant 1

HCID 90987543Tert-butyl[2-(5-ethyloxycarbonyl-pentylsulfanyl)-benzoimidazol-1-yl]-acetate

Product 1

HCID 11660316[2-(5-Ethyloxycarbonyl-pentylsulfanyl)-benzoimidazol-1-yl]-acetic acidYield 85%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl[2-(5-ethyloxycarbonyl-pentylsulfanyl)-benzoimidazol-1-yl]-acetate (Precursor E-01b, 44 mg, 0.11 mmol) in TFA/dichloromethane (1:1, 2 ml) is stirred at rt for 3 h. The solvents are removed under a stream of air. The solid residue is suspended in Et2O (2 ml) and sonicated. Filtration, rinsing with Et2O and drying under high vacuum yields the title compound (32 mg) as a white solid in 85% yield: tR=5.33 min (LC-1), ESI-MS (pos.): m/z 351.07 [M+H]+, ESI-MS (neg.): m/z 349.22 [M−H]+; 1H-NMR (CDCl3): δ (ppm) 1.25 (t, 3H CH3), 1.44 (s, 9H, tBu), 1.32-1.44 (m, 2H), 1.52-1.70 (m, 4H), 2.24 (t, 2H, CH2C═O), 3.24 (t, 2H, SCH2), 4.10 (q, 2H, OCH2), 4.15 (br. s, 1H, CO2H), 4.86 (s, 2H, CH2CO2), 7.24 (s, 3Harom), 7.63 (m, 1Harom).

Workup

  1. customThe solvents are removed under a stream of air
  2. customsonicated
  3. filtrationFiltration
  4. washrinsing with Et2O
  5. customdrying under high vacuum

Sources & evidence

ORD record
ord-3f4b9e44b5ae4be7832c74bcf1d7cab1
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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