Triethylamine → Benzimidazole

HRID 222869Notes

Reaction equation

HRID 222869 reaction equation
[NH2:1][C@H:2](C(N)=O)[CH2:3][C:4]1C=CC(O)=C[CH:5]=1.Cl.C([N:17]([CH2:20]C)[CH2:18][CH3:19])C>O1CCOCC1>[N:17]1[C:18]2[CH:19]=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][CH:20]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 45157672L-Tyrosinamide--hydrogen chloride (1/1)

Product 1

HCID 5798BenzimidazoleYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a room temperature solution of intermediate 2 in anhydrous dioxane (200 mL) were added triethylamine (6 mL, 40 mmol) and tert-butyldimethylsilyltrifluoro methanesulfonate (8.6 g, 32 mmol). The resulting solution was then stirred overnight and quenched with saturated aqueous sodium bicarbonate solution. It was extracted with dichloromethane (3×100 mL), and the combined organic layers were dried over sodium sulfate and concentrate in vacuo. The residue was purified by flash chromatography (silica gel, hexane/ethyl acetate) to provide intermediate 3 (9.2 g, 72% overall), which was characterized by LC/MS (LRMS (M+H+) m/z: 458.16).

Workup

  1. customquenched with saturated aqueous sodium bicarbonate solution
  2. extractionIt was extracted with dichloromethane (3×100 mL)
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrate in vacuo
  5. customThe residue was purified by flash chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ddd7e7e3207340729a7a5ec54e0fcf0e
Source dataset
uspto-grants-2012_06
Patent number
US08207340B2

Reaction notes

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