Water → N-Fmoc-3-fluoro-L-tyrosine

HRID 1482236Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1482236
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([F:14])[CH:8]=1)[C:3]([OH:5])=[O:4].[CH:15]1[C:27]2[CH:26]([CH2:28][O:29][C:30](ON3C(=O)CCC3=O)=[O:31])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1.O>C(=O)([O-])[O-].[Na+].[Na+]>[CH:15]1[C:27]2[CH:26]([CH2:28][O:29][C:30]([NH:1][C@@H:2]([CH2:6][C:7]3[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([F:14])[CH:8]=3)[C:3]([OH:5])=[O:4])=[O:31])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 6433303-Fluoro-L-tyrosine

Produkt 1

HCID 89668487N-Fmoc-3-fluoro-L-tyrosineAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

(S)-2-Amino-3-(3-fluoro-4-hydroxyphenyl)propanoic acid (H-Tyr(3-F)-HH, SP449) (7.2 g, 36.2 mmol) was dissolved in a 10% aqueous sodium carbonate solution (250 ml), N-(9-fluorenylmethoxycarbonyloxy)-succinimide (12.2 g, 36.2 mmol) was added and the mixture was stirred at room temperature for 1.5 hours. Water (120 ml) was added to the reaction solution, and the mixture was then washed with 200 ml of diethyl ether twice and with 100 ml of diethyl ether once. The aqueous layer was made acidic (pH=2) by adding a 6 N aqueous HCl solution thereto, and then extracted with 250 ml of ethyl acetate twice and with 200 ml of ethyl acetate once. The resulting ethyl acetate layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford the title compound (SP450, 15.3 g, 100%).

Aufarbeitung

  1. additionwas added
  2. washthe mixture was then washed with 200 ml of diethyl ether twice
  3. additionby adding a 6 N aqueous HCl solution
  4. extractionextracted with 250 ml of ethyl acetate twice
  5. dry with materialThe resulting ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dd12125ec0074acf87bc2a94b40b9814
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409952B2

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