HCID 90961260, compound → [2-(3-Methoxycarbonyl-benzylsulfanyl)-benzoimidazol-1-yl]-acetic acid

HRID 2389479Notes

Reaction equation

HRID 2389479 reaction equation
C([O:5][C:6](=[O:29])[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][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH:20]=1)(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[CH3:28][O:27][C:25]([C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[CH2:18][S:17][C:9]1[N:8]([CH2:7][C:6]([OH:29])=[O:5])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=1)=[O:26]

Participants

3

Reactant 1

HCID 90961260HCID 90961260, compound

Product 1

HCID 11610095[2-(3-Methoxycarbonyl-benzylsulfanyl)-benzoimidazol-1-yl]-acetic acidYield 73.3%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl[2-(3-methoxycarbonyl-benzylsulfanyl)-benzoimidazol-1-yl]-acetate (Precursor H-01b, 31 mg, 0.075 mmol) in TFA/dichloromethane (1:1, 2 ml) is stirred at rt for 4 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 (19.6 mg) in 73% as a white solid: tR=5.52 min (LC-1), ESI-MS (pos.): m/z 357.25 [M+H]+, ESI-MS (neg.): m/z 355.29 [M−H]+; 1H-NMR (DMSO-d6): δ (ppm) 3.83 (s, 3H, OMe), 4.65 (s, 2H, SCH2), 4.92 (s, 1H, CH2CO2), 7.15-7.21 (m, 2Harom), 7.42-7.48 (m, 2Harom), 7.57 (m, 1Harom), 7.72 (d, 1Harom), 7.81 (d, 1Harom), 8.05 (s, 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-768a767bee894c07b1dd4b47130520ef
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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