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L-Homoserine → (2S)-2-(((9H-fluoren-9-ylmethoxy)carbonyl)amino)-4-hydroxybutanoic acid

HRID 62435
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 62435
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5].C([O-])(O)=O.[Na+].[C:14](ON1C(=O)CCC1=O)([O:16][CH2:17][CH:18]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15].CCOCC.O>O.CC(C)=O>[C:14]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5])([O:16][CH2:17][CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[C:30]1=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 12647L-HomoserineHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 516892Sodium BicarbonateHCID 21584184Diethylether water

Produkt 1

HCID 15449971(2S)-2-(((9H-fluoren-9-ylmethoxy)carbonyl)amino)-4-hydroxybutanoic acidAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180
Acetone
Lösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

L-homoserine (15 g, MW119.12, 0.126 mol) and NaHCO3 (22 g, MW84, 0.26 mol) were dissolved in water (600 mL). The solution was chilled in an ice bath, followed by addition of Fmoc-OSu (42.5 g, MW337.3, 0.126 mol) in acetone (400 mL). The mixture was stirred overnight. A mixture of ether/water (200 mL/200 mL) was added, and the solid was filtered off. The filtrate was separated and the aqueous phase was washed with ethyl twice (100 mL×2), followed by acidifying with 3N HClaq (about 100 mL) to pH3-4. The suspension was extracted with ether (200 mL×2). The combined organic phases were washed with brine once (100 mL) and dried over Na2SO4. After evaporation, white solid was obtained (weight: 38 g, yield: 88%).

Aufarbeitung

  1. temperatureThe solution was chilled in an ice bath
  2. additionwas added
  3. filtrationthe solid was filtered off
  4. customThe filtrate was separated
  5. washthe aqueous phase was washed with ethyl twice (100 mL×2)
  6. extractionThe suspension was extracted with ether (200 mL×2)
  7. washThe combined organic phases were washed with brine once (100 mL)
  8. dry with materialdried over Na2SO4
  9. customAfter evaporation
  10. customwhite solid was obtained (weight: 38 g, yield: 88%)

Quellen und Nachweise

ORD-Eintrag
ord-13d45cf8286f4c1b922e0a1388f241ba
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09446157B2

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