Trifluoroacetic acid → Ethyl 2-amino-3-(3-(benzyloxy)phenyl)propanoate

HRID 2403238Notes

Reaction equation

HRID 2403238 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH:16]([NH:22]C(OC(C)(C)C)=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:22][CH:16]([CH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71208957Ethyl 3-(3-(benzyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoate

Product 1

HCID 4014929Ethyl 2-amino-3-(3-(benzyloxy)phenyl)propanoateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

159 (850 mg) was dissolved in 4 ml of DCM and 4 ml of TFA was added then the reaction mixture was let 1 h at room temperature. The reaction mixture is concentrated and 50 ml of AcOEt are added. The organic phase are washed with saturated NaHCO3 and brine then dried over Na2SO4, filtered and concentrated to afford 160 as a white solid (540 mg, 86%). 1H NMR (DMSO): δ 1.26 (t, 3H, J=6.5 Hz), 1.89 (s, 2H), 2.89 (dd, 1H, J=13.1, 6.1 Hz), 2.97 (dd, 1H, J=13.1, 6.1 Hz), 3.68 (t, 1H, J=6.1 Hz), 4.16 (q, 2H, J=6.5 Hz), 5.21 (s, 2H), 6.90 (d, 1H, J=7.6 Hz), 6.99 (s, 2H), 7.32 (t, 1H, J=7.8 Hz), 7.47 (m, 1H), 7.53 (t, 2H, J=7.0 Hz), 7.58 (d, 2H, J=7.6 Hz).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. addition50 ml of AcOEt are added
  3. washThe organic phase are washed with saturated NaHCO3 and brine
  4. dry with materialthen dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e1598b864e9c4579a179f3e9d86d2807
Source dataset
uspto-grants-2014_08
Patent number
US08802666B2

Reaction notes

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