Cesium carbonate → tert-Butyl {2-[3-(tert-butoxycarbonyl-phenethyl-amino)-propylsulfanyl]-benzoimidazol-1-yl}-acetate

HRID 2389485Notes

Reaction equation

HRID 2389485 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:9][CH2:10][CH2:11][S:12][C:13]1[NH:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].C(=O)([O-])[O-].[Cs+].[Cs+].CNCCS>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:9][CH2:10][CH2:11][S:12][C:13]1[N:17]([CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[N:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 202285Ethanethiol, 2-(methylamino)-HCID 693165952-[3-(tert-Butoxycarbonyl-phenethyl-amino)-propylsulfanyl]-benzoimidazole

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[3-(tert-Butoxycarbonyl-phenethyl-amino)-propylsulfanyl]-benzoimidazole (Precursor J-01c, 239 mg, 0.58 mmol), tert-butyl bromoacetate (136 mg, 103 μl, 0.70 mmol) and cesium carbonate (227 mg, 0.70 mmol) are dissolved in dry DMF (6 ml) and allowed to stir for 1 h at rt. N-(2-Mercaptoethyl)aminomethyl polystyrene (1.4 mmol/g, 0.5 g, 0.36 mmol) is added and the crude mixture is stirred at rt for 1 h. After filtration and removal of the solvent in vacuo, the crude product is diluted in dichloromethane, washed with a 10% aqueous citric acid solution and with a saturated aqueous NaHCO3 solution. The organic phase is dried over MgSO4 and the solvent evaporated in vacuo, yielding the title compound: tR=2.79 min (LC-2), ESI-MS (neg.): m/z 526.61 [M−H]+; 1H-NMR (CDCl3): δ (ppm) 1.46 (s, 18H, 2×tBu), 2.00 (m, 2H, SCH2CH2), 2.85 (m, 2H, CH2Ph), 3.26-3.85 (m, 6H), 4.77 (s, 2H, CH2CO2), 7.44-7.59 (m, 8Harom), 7.94 (m, 1Harom).

Workup

  1. filtrationAfter filtration and removal of the solvent in vacuo
  2. additionthe crude product is diluted in dichloromethane
  3. washwashed with a 10% aqueous citric acid solution and with a saturated aqueous NaHCO3 solution
  4. dry with materialThe organic phase is dried over MgSO4
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-06d0931d977c475fbfe014e520a48386
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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