Trifluoroacetic acid → Ethyl 3-(2-aminoethyl)-5-[(4-fluorophenyl)methyl]benzenepropanoate

HRID 53331Notes

Reaction equation

HRID 53331 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:14]=[C:15]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:16]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:14]=[C:15]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19962360Ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzenepropanoate

Product 1

HCID 19962359Ethyl 3-(2-aminoethyl)-5-[(4-fluorophenyl)methyl]benzenepropanoateYield 62.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 3-[2-(t-butoxycarbonylamino)ethyl]-5-[(4-fluorophenyl)methyl]benzene-propanoate (2.36 g) and trifluoracetic acid (5 ml) in dichloromethane (25 ml) was allowed to stand at room temperature overnight and then evaporated. The residue was partitioned between ether and dilute sodium hydroxide solution. The organic layer was separated, washed with water and dried (MgSO4). The solvent was evaporated and the residue chromatographed on silica eluting with mixtures of dichloromethane, methanol and concentrated ammonium hydroxide. The product containing fractions were combined and the solvent evaporated to give the title compound as a gum (1.13 g), Rf 0.1 (SS 4). N.M.R. δ(CDCl3): 1.24 (3H,t), 1.48(2H,s), 2.61(2H,t), 2.73(2H,t), 2.90-2.98(4H,m), 3.93(2H,s), 4.14(2H,q), 6.88(2H,s), 6.91(1H,s), 6.96-7.03(2H,m), 7.12-7.18(2H,m).

Workup

  1. customevaporated
  2. customThe residue was partitioned between ether and dilute sodium hydroxide solution
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residue chromatographed on silica eluting with mixtures of dichloromethane, methanol and concentrated ammonium hydroxide
  8. additionThe product containing fractions
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-e7b7a65f6f53451292f633d85295d156
Source dataset
uspto-grants-1997_04
Patent number
US05618941

Reaction notes

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