Tert-butyl[2-(2-methoxy-benzylsulfanyl)-benzoimidazol-1-yl]-acetate → [2-(2-Methoxy-benzylsulfanyl)-benzoimidazol-1-yl]-acetic acid

HRID 2389468Notes

Reaction equation

HRID 2389468 reaction equation
C([O:5][C:6](=[O:27])[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]=[CH:21][C:20]=1[O:25][CH3:26])(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[CH3:26][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][S:17][C:9]1[N:8]([CH2:7][C:6]([OH:27])=[O:5])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=1

Participants

3

Reactant 1

HCID 90907082Tert-butyl[2-(2-methoxy-benzylsulfanyl)-benzoimidazol-1-yl]-acetate

Product 1

HCID 69318939[2-(2-Methoxy-benzylsulfanyl)-benzoimidazol-1-yl]-acetic acidYield 97.4%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl[2-(2-methoxy-benzylsulfanyl)-benzoimidazol-1-yl]-acetate (Precursor C-01b, 20 mg, 0.05 mmol) is stirred in TFA/dichloromethane (1:1, 4.0 ml) at rt overnight. The volatiles are removed in vacuo and the residue is dried under high vacuum, yielding the title compound (16.0 mg) in 94% as a white solid: tR=5.27 min (LC-1), MS (pos.): m/z 329.22 [M+H]+, MS (neg.): m/z 327.20 [M−H]+; 1H-NMR (DMSO-d6): δ (ppm) 3.82 (s, 3H, OCH3), 4.51 (s, 2H, SCH2), 4.92 (s, 2H, CH2CO2), 6.89 (t, 1Harom), 7.04 (d, 1Harom), 7.18 (m, 2Harom), 7.30 (t, 1Harom), 7.40 (d, 1Harom), 7.50 (m, 1Harom), 7.61 (m, 1Harom).

Workup

  1. customThe volatiles are removed in vacuo
  2. customthe residue is dried under high vacuum

Sources & evidence

ORD record
ord-c88565cbafc641699c7eb6fc4b87406a
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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