Potassium Carbonate → [(S)-1-(6-ethynyl-1H-benzoimidazol-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

HRID 227163Notes

Reaction equation

HRID 227163 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C@H:8]([C:16]1[NH:20][C:19]2[CH:21]=[C:22]([C:25]#[C:26][Si](C)(C)C)[CH:23]=[CH:24][C:18]=2[N:17]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5][C:6](=[O:31])[NH:7][C@H:8]([C:16]1[NH:20][C:19]2[CH:21]=[C:22]([C:25]#[CH:26])[CH:23]=[CH:24][C:18]=2[N:17]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66815258[(S)-2-phenyl-1-(6-trimethylsilanylethynyl-1H-benzoimidazol-2-yl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 86627923[(S)-1-(6-ethynyl-1H-benzoimidazol-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [(S)-2-Phenyl-1-(6-trimethylsilanylethynyl-1H-benzoimidazol-2-yl)-ethyl]-carbamic acid tert-butyl ester (90 mg, 0.208 mmol) in methanol (10 mL) at room temperature, was added finely powdered anhydrous potassium carbonate (258 mg, 1.87 mmol). The resulting heterogenous mixture was stirred at room temperature until LC/MS indicated the reaction was complete. The solvent was then allowed to evaporate and resulting residue was partitioned in 1:1 v/v water/ethyl acetate (50 mL total volume) and the aqueous layer was separated and extracted twice with ethyl acetate (20 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The yellowish colored residue was applied to a silica gel column using dichloromethane (10 mL) and gradient eluted from 10 to 75% v/v ethyl acetate in hexanes to give [(S)-1-(6-ethynyl-1H-benzoimidazol-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester (54 mg, 72%)

Workup

  1. customto evaporate
  2. customresulting residue
  3. customwas partitioned in 1:1 v/v water/ethyl acetate (50 mL total volume)
  4. customthe aqueous layer was separated
  5. extractionextracted twice with ethyl acetate (20 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washgradient eluted from 10 to 75% v/v ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7b84682a75da435cb689e4cef660c4b6
Source dataset
uspto-grants-2009_07
Patent number
US07557221B2

Reaction notes

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