DL-beta-Phenylalanine → 3-(4-Methylphthalimido)-3-phenylpropionic acid

HRID 1940076

Reaktionsgleichung

Reaktionsgleichung von HRID 1940076
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][CH:12]=1.[NH2:13][CH:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:15][C:16]([OH:18])=[O:17]>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:13]([CH:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][C:16]([OH:18])=[O:17])[C:6](=[O:8])[C:5]2=[CH:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 69189DL-beta-PhenylalanineHCID 880694-Methylphthalic anhydride

Produkt 1

HCID 212509643-(4-Methylphthalimido)-3-phenylpropionic acidAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A stirred mixture of 4-methylphthalic acid anhydride (1.62 g, 10.0 mmol) and 3-amino-3-phenylpropionic acid (1.65 g, 10.0 mmol) in 15 mL of acetic acid under nitrogen was heated to reflux for 6 hours. The resulting reaction solution was concentrated in vacuo to an oil which was crystallized from 20 mL of a 1/1 mixture of ethyl acetate/hexane to afford 1.69 g (55%) of 3-(4-methylphthalimido)-3-phenylpropionic acid as an off-white powder: 1H NMR (DMSO-d6) δ12.5 (br s, 1H, COOH), 7.85-7.55 (m, 3 H, Ar), 7.55-7.2 (m, 5H, Ar), 5.68 (dd, 1H, J=9, 7 Hz, CH), 3.51 (dd, 1H, J=9, 16.5 Hz), 3.29 (dd, 1H, J=9, 16.5 Hz), 2.47 (s, 3H, CH3). Anal. Calcd for C18H15N1O4Theory; C, 69.89,H, 4.89, N, 4.53. Found: C, 69.45,H, 4.93, N, 4.55. HPLC: 95%.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 6 hours
  3. customThe resulting reaction solution
  4. concentrationwas concentrated in vacuo to an oil which
  5. customwas crystallized from 20 mL of a 1/1 mixture of ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-7fcfc7d99e2340b08ec7fdefbdb3505c
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05698579

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