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

HRID 1397874Notes

Reaction equation

HRID 1397874 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH:16]([NH:27]C(OC(C)(C)C)=O)[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[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>[NH2:27][CH:16]([CH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)[C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22623796Benzyl 3-(3-(benzyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoate

Product 1

HCID 67257589Benzyl 2-amino-3-(3-(benzyloxy)phenyl)propanoateYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

172 (610 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. The crude product was purified by flash chromatography (AcOEt/Hexane 2/8) to afford 173 as white solid (480 mg, 85%). 1H NMR (DMSO): δ 2.90 (m, 2H), 3.73 (t, 1H, J=7.4 Hz), 5.19 (s, 4H), 6.70 (d, 1H, J=7.3 Hz), 6.74 (m, 2H), 6.97 (m, 1H), 7.17 (t, 1H, J=7.9 Hz), 7.41 (d, 2H, J=6.5 Hz), 7.48 (m, 2H), 9.37 (s, 2H).

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
  7. customThe crude product was purified by flash chromatography (AcOEt/Hexane 2/8)

Sources & evidence

ORD record
ord-a717b8dd65da40cd9edf6121f5c0ba44
Source dataset
uspto-grants-2014_12
Patent number
US08901295B2

Reaction notes

Loading…