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

HRID 1397867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397867
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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 (5, 2H), 2.89 (dd, 1H, 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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-16dbc974f31f4d19894cb08bd487a986
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901295B2

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