Allyl bromide → (R)-3-(4-Allyloxy-3-fluorophenyl)-2-tert-butoxycarbonylaminopropionic acid

HRID 2274551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2274551
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([F:23])[CH:17]=1)[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:24](Br)[CH:25]=[CH2:26]>CN(C=O)C>[CH2:26]([O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C@@H:11]([NH:10][C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:9])[C:12]([OH:14])=[O:13])=[CH:17][C:18]=1[F:23])[CH:25]=[CH2:24]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 40429673N-Boc-3-fluoro-D-tyrosine

Produkt 1

HCID 67028604(R)-3-(4-Allyloxy-3-fluorophenyl)-2-tert-butoxycarbonylaminopropionic acidAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1.18 g (60%, 29.39 mmol) of sodium hydride were added to a solution of 4.0 g (13.36 mmol) of (R)-2-tert-butoxycarbonylamino-3-(3-fluoro-4-hydroxyphenyl)propionic acid in 23 ml of DMF while stirring at 0° C., and the mixture was stirred at this temperature. After 15 min, 1.27 ml (1.78 g, 14.7 mmol) of allyl bromide were added, and stirring was continued for 1 h while the mixture reached RT. It was quenched with methanol and, after cooling, excess methanol was removed in a rotary evaporator. Dilution with diethyl ether was followed by acidification with 1N hydrochloric acid, and the aqueous phase was extracted twice more with diethyl ether, and the combined organic phases were washed with saturated sodium chloride solution, dried over NaSO4, filtered and concentrated. 4.50 g of a yellowish oil were obtained.

Aufarbeitung

  1. stirringthe mixture was stirred at this temperature
  2. stirringstirring
  3. waitwas continued for 1 h while the mixture
  4. customreached RT
  5. customIt was quenched with methanol
  6. temperatureafter cooling
  7. customexcess methanol was removed in a rotary evaporator
  8. extractionthe aqueous phase was extracted twice more with diethyl ether
  9. washthe combined organic phases were washed with saturated sodium chloride solution
  10. dry with materialdried over NaSO4
  11. filtrationfiltered
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-22ac12946ec046fdb648636924b417f1
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126955B2

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