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2-Butene, 1,4-dibromo- → (2S,7S,E)-1,8-Bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-2,7-diisopropyloct-4-ene-1,8-dione

HRID 1452116
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1452116
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:11]([C@H:18]1[CH2:22][O:21][C:20](=[O:23])[N:19]1[C:24](=[O:29])[CH2:25][CH:26]([CH3:28])[CH3:27])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Br[CH2:31][CH:32]=[CH:33][CH2:34]Br.[Cl-].[NH4+:37]>O1CCCC1.CN1CCCN(C)C1=O>[CH2:11]([C@H:18]1[CH2:22][O:21][C:20](=[O:23])[N:19]1[C:24](=[O:29])[C@H:25]([CH:26]([CH3:27])[CH3:28])[CH2:31]/[CH:32]=[CH:33]/[CH2:34][C@@H:25]([CH:26]([CH3:28])[CH3:27])[C:24]([N:37]1[C@@H:18]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:22][O:21][C:20]1=[O:23])=[O:29])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 131802-Butene, 1,4-dibromo-HCID 25517Ammonium ChlorideHCID 2733832Lithium hexamethyldisilazaneHCID 11108107(4S)-4-Benzyl-3-isovaleryloxazolidin-2-one

Produkt 1

HCID 22870117(2S,7S,E)-1,8-Bis((S)-4-benzyl-2-oxooxazolidin-3-yl)-2,7-diisopropyloct-4-ene-1,8-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Lösungsmittel

Reaktionsbedingungen

Temperatur
-75 °C

Versuchsvorschrift

With stirring at -75° C., 48 ml of a 1.0M solution of lithium hexamethyldisilazide in tetrahydrofuran are added dropwise in the course of 1 hour to a solution of 11.5 g of 4(S)-benzyl-3-isovaleroyl-oxazolidin-2-one in 32 ml of tetrahydrofuran. The reaction mixture is stirred further for 2 hours at -75° C. and for 20 minutes at -20° C., then 10 ml of 1,3-dimethyl-3,4,5,6-tetrahydro- -2-(1H)-pyrimidone (DMPU) and, in the course of 45 minutes, a solution of 4.28 g of 1,4-dibromo-2-butene in 10 ml of tetrahydrofuran are added thereto. The reaction mixture is stirred further for 15 hours at -20° C., and then in the course of 1 hour brought to 0° C. At -20° C., 10 ml of saturated ammonium chloride solution are then added thereto and after 15 minutes the reaction mixture is brought to room temperature. The reaction mixture is then partitioned between dichloromethane and saturated sodium chloride solution/water (1:1). The organic phases are combined, dried over sodium sulfate and concentrated by evaporation and the residue is purified by means of FC (hexane/ethyl acetate 4:1) to yield the title compound: Rf (hexane/ethyl acetate 4:1)=0.30; m.p.=110°-111° C. (crystallised from ethyl acetate/hexane).

Aufarbeitung

  1. stirringThe reaction mixture is stirred further for 2 hours at -75° C. and for 20 minutes at -20° C.
  2. stirringThe reaction mixture is stirred further for 15 hours at -20° C.
  3. customin the course of 1 hour
  4. custombrought to 0° C
  5. customThe reaction mixture is then partitioned between dichloromethane and saturated sodium chloride solution/water (1:1)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated by evaporation
  8. customthe residue is purified by means of FC (hexane/ethyl acetate 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-836f94c523eb4c46afe70b34f05a1c02
Quelldatensatz
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05606078

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