Trifluoroacetic acid → HCID 54133431, compound

HRID 564937Notes

Reaction equation

HRID 564937 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]([C:20]1[CH:32]=[CH:31][C:23]([CH:24]=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=1)[CH2:16][CH2:17][O:18][CH3:19])=O)(C)(C)C>>[CH3:19][O:18][CH2:17][CH2:16][NH:15][C:20]1[CH:32]=[CH:31][C:23]([CH:24]=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53821831HCID 53821831, compound

Product 1

HCID 54133431HCID 54133431, compoundYield 70.7%

Procedure

Trifluoroacetic acid (3 ml) was added to ethyl 4-[N-tert-butoxycarbonyl-N-(2-methoxyethyl)amino]cinnamate (932 mg) in ice water bath and stirred for 15 minutes at same temperature. The solvent was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacua. The residue was chromatographed on silica gel eluting to a mixture of n-hexane and ethyl acetate (3:1) and recrystallized from a mixture of n-hexane and ethyl acetate to give ethyl 4-(2-methoxyethylamino)cinnamate (470 mg) as crystals.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacua
  6. customThe residue was chromatographed on silica gel eluting to a mixture of n-hexane and ethyl acetate (3:1)
  7. customrecrystallized from a mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-05510fa5f44b4f238ade17e1fb126022
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Reaction notes

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