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Ammonium Chloride → 3-[2(S)-Ethyl-3-(4-propyloxymethyl-naphth-2-yl)-propionyl]-4(R)-benzyl-oxazolidin-2-one

HRID 744778
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 744778
[C:1]([N:6]1[C@H:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][O:8][C:7]1=[O:18])(=[O:5])[CH2:2][CH2:3][CH3:4].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:29]([O:32][CH2:33][C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[C:36]([CH2:44]Br)[CH:35]=1)[CH2:30][CH3:31].[Cl-].[NH4+]>O1CCCC1>[CH2:3]([C@@H:2]([CH2:44][C:36]1[CH:35]=[C:34]([CH2:33][O:32][CH2:29][CH2:30][CH3:31])[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=1)[C:1]([N:6]1[C@H:10]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:9][O:8][C:7]1=[O:18])=[O:5])[CH3:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium hexamethyldisilazaneHCID 11736739(4R)-4-benzyl-3-butanoyl-1,3-oxazolidin-2-oneHCID 214587034-Propoxymethyl-2-bromomethylnaphthalene

Produkt 1

HCID 228657673-[2(S)-Ethyl-3-(4-propyloxymethyl-naphth-2-yl)-propionyl]-4(R)-benzyl-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-75 °C

Versuchsvorschrift

30 ml of tetrahydrofuran and a solution of 2.97 g of 3-butyroyl-4(R)-benzyl-oxazolidin-2-one in 15 ml of tetrahydrofuran are added dropwise in succession to a solution, stirred at -75° C., of 12 ml of 1M lithium hexamethyldisilazide solution. The reaction mixture is stirred for 1 hour at -75° C., a solution of 3.52 g of 4-propoxymethyl-2-bromomethyl-naphthalene in 15 ml of tetrahydrofuran is added dropwise thereto and the mixture is then stirred further for 1 hour at -30° C. and for 3 hours at 0° C. After the dropwise addition at 0° C. of 2.7 ml of saturated ammonium chloride solution, the reaction mixture is concentrated by evaporation and the residue is partitioned between diethyl ether and water. The organic extracts are concentrated by evaporation and the residue is purified by FC (1 kg of silica gel, eluant: dichloromethane/hexane=3:1), yielding the title compound: Rf (dichloromethane/hexane=3:1)=0.24; FAB-MS (M+Na)+ =482.

Aufarbeitung

  1. stirringthe mixture is then stirred further for 1 hour at -30° C. and for 3 hours at 0° C
  2. concentrationthe reaction mixture is concentrated by evaporation
  3. customthe residue is partitioned between diethyl ether and water
  4. concentrationThe organic extracts are concentrated by evaporation
  5. customthe residue is purified by FC (1 kg of silica gel, eluant: dichloromethane/hexane=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-8002bd28e7134beead23cd6fc049c856
Quelldatensatz
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05559111

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