Sodium Hydroxide → 2-(1-Trityl-1H-imidazol-4-yl)-ethylamine

HRID 412168Notes

Reaction equation

HRID 412168 reaction equation
[C:1]1([C:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][NH:15]C(=O)C(F)(F)F)[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:28]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][NH2:15])[N:10]=[CH:9]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 110377171-(Triphenylmethyl)-4-[2-(trifluoroacetamido)-1-ethyl]imidazole

Product 1

HCID 6183402-(1-Trityl-1H-imidazol-4-yl)-ethylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of the product from Step A (48.8 g, 109 mmol) in 1L of methanol was added 1M sodium hydroxide solution (325 mL, 325 mmol). Over the course of four days, additional methanol (3 L) and sodium hydroxide solution (325 mL, 325 mmol) were added. The solution was concentrated in vacuo, and partitioned between EtOAc and water. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the titled product.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c59ea682f89c4f60ab0002448724a62f
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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