Hydrochloric Acid → [3-(1-tert-Butoxycarbonylmethyl-1H-benzoimidazol-2-ylsulfanyl)-propyl]-phenethyl-ammonium chloride

HRID 2389495Notes

Reaction equation

HRID 2389495 reaction equation
C(OC([N:8]([CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:9][CH2:10][CH2:11][S:12][C:13]1[N:17]([CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:16]2[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=2[N:14]=1)=O)(C)(C)C.[ClH:38]>C(OCC)(=O)C>[Cl-:38].[C:22]([O:21][C:19]([CH2:18][N:17]1[C:16]2[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=2[N:14]=[C:13]1[S:12][CH2:11][CH2:10][CH2:9][NH2+:8][CH2:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86620029tert-Butyl {2-[3-(tert-butoxycarbonyl-phenethyl-amino)-propylsulfanyl]-benzoimidazol-1-yl}-acetate

Product 1

HCID 69318458[3-(1-tert-Butoxycarbonylmethyl-1H-benzoimidazol-2-ylsulfanyl)-propyl]-phenethyl-ammonium chloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl {2-[3-(tert-butoxycarbonyl-phenethyl-amino)-propylsulfanyl]-benzoimidazol-1-yl}-acetate (Precursor J-01b, 199 mg, 0.38 mmol) is dissolved in a 1M HCl solution in ethyl acetate (1.89 ml). The resulting solution is stirred at rt for 1 h. The solvent is evaporated and the crude solid is dissolved in dichloromethane, the resulting organic phase is washed with a saturated aqueous NaHCO3 solution and with water. Evaporation of the solvent in vacuo and chromatography of the residue on silica-gel (dichloromethane/MeOH, 92:8) yields the title compound (107 mg) in 61% as a white solid: tR=2.62 min (LC-2), ESI-MS (pos.): m/z 510.49 [M+H]+.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe crude solid is dissolved in dichloromethane
  3. washthe resulting organic phase is washed with a saturated aqueous NaHCO3 solution and with water
  4. customEvaporation of the solvent in vacuo and chromatography of the residue on silica-gel (dichloromethane/MeOH, 92:8)

Sources & evidence

ORD record
ord-b1e6b69b768d4f34b7f2bff7f898952d
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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