Water → N-Phthaloyl-DL-phenylalanine

HRID 1417368Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1417368
[NH2:1][CH:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:13](=[O:16])([O-])[O-].[Na+].[Na+].[OH2:19]>>[C:13]1(=[O:16])[N:1]([CH:2]([CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([OH:12])=[O:11])[C:3](=[O:19])[C:4]2=[CH:9][CH:8]=[CH:7][CH:6]=[C:5]12

Komponenten

4

Edukt 3

HCID 962WaterHCID 994Dl-PhenylalanineHCID 10340Sodium Carbonate

Produkt 1

HCID 227754N-Phthaloyl-DL-phenylalanineAusbeute 74 %

Versuchsvorschrift

To a stirred solution of d,1-phenylalanine (4.17 g, 25.0 mmol) and sodium carbonate (2.78 g, 26.25 mmol) in 50 mL of water is added N-carboethoxyphthallmde (5.65 g, 25.0 mmol). The resulting slurry is stirred for 1.5 hour and filtered. The pH of the filtrate is adjusted to 1-2 with 4N hydrochloric acid with stirring. After 20 minutes, the slurry is refiltered and the solid washed with water. The solid is dried in vacuo (60° C., <1 mm) to afford 5.44 g (74%) of 2-phthalimido-3-phenylpropionic acid as a white powder: mp 165°-169° C.; 1H NMR (DMSO-d6, 250 M Hz) δ 12.5(br s, 1H), 7.84(s, 4H), 7.23-7.06 (m, 5H), 5.13 (dd, 1H, J=5.0), 3.26-3.05 (m, 2H); 13C NMR (250 MHz, DMSO-d6) δ 170.0, 167.0, 137.2, 134.8, 130.6, 128.6, 128.2, 126.5, 123.3, 52.8, 33.8. Anal. Calculated for C17H13NO4. Theoretical: C, 69.15; H, 4.44; N, 4.74. Found: C, 69.07; H, 4.34; N, 4.78.

Aufarbeitung

  1. filtrationfiltered
  2. stirringwith stirring
  3. waitAfter 20 minutes
  4. washthe solid washed with water
  5. customThe solid is dried in vacuo (60° C., <1 mm)

Quellen und Nachweise

ORD-Eintrag
ord-86f7be88116d464bb80e781c76732ca8
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05877200

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