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

HRID 2403245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2403245
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 67257589Benzyl 2-amino-3-(3-(benzyloxy)phenyl)propanoateAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

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

Quellen und Nachweise

ORD-Eintrag
ord-de97aec734d247ee84703d36a6774551
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802666B2

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