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Ethyl Acetate → 3-Cyclopentyl-5-(3-furan-2-yl-propionylamino)-3-hydroxy-pentanoic acid ethyl ester

HRID 1453338
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1453338
[Li+].CC([N-]C(C)C)C.[CH3:9][CH2:10][O:11][C:12]([CH3:14])=[O:13].[CH:15]1([C:20](=[O:33])[CH2:21][CH2:22][NH:23][C:24](=[O:32])[CH2:25][CH2:26][C:27]2[O:28][CH:29]=[CH:30][CH:31]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1>C1COCC1>[CH:15]1([C:20]([OH:33])([CH2:21][CH2:22][NH:23][C:24](=[O:32])[CH2:25][CH2:26][C:27]2[O:28][CH:29]=[CH:30][CH:31]=2)[CH2:14][C:12]([O:11][CH2:10][CH3:9])=[O:13])[CH2:16][CH2:17][CH2:18][CH2:19]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 2724682Lithium diisopropylamideHCID 58762649N-(3-Cyclopentyl-3-oxo-propyl)-3-furan-2-yl-propionamide

Produkt 1

HCID 587623263-Cyclopentyl-5-(3-furan-2-yl-propionylamino)-3-hydroxy-pentanoic acid ethyl esterAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

To a solution of LDA (1.0 M, 1.1 mL, 1.1 mmol) cooled to −78° C. was added EtOAc (0.1 mL, 1.1 mmol). After stirring for 30 minutes, a solution of N-(3-cyclopentyl-3-oxo-propyl)-3-furan-2-yl-propionamide (100 mg, 0.38 mmol; described in Step 2 of example H(4)) dissolved in 3 mL THF was added. The reaction was stirred for 2 hours and then allowed to warm to −40° C. The reaction was quenched with 10 mL saturated NH4Cl, and the layers were separated. The aqueous layer was extracted with 3×10 mL CH2Cl2, and the organic layers were combined. After concentrating the organic layers by rotary evaporation, the product was purified by flash chromatography (86 mg, 64% yield). MS (ESI): 350 (M−H).

Aufarbeitung

  1. additionwas added
  2. stirringThe reaction was stirred for 2 hours
  3. customThe reaction was quenched with 10 mL saturated NH4Cl
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with 3×10 mL CH2Cl2
  6. concentrationAfter concentrating the organic layers
  7. customby rotary evaporation
  8. customthe product was purified by flash chromatography (86 mg, 64% yield)

Quellen und Nachweise

ORD-Eintrag
ord-f0556be263c04f218456b6ae0ae71cdf
Quelldatensatz
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07473790B2

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