Hydrochloric Acid → (5R)-3-[6-(But-3-ynyloxy)hexyl]5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 750445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 750445
[CH3:1][C:2]1([CH3:18])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[NH:14][CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.[H-].[Na+].[CH2:21]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br)[CH2:22][C:23]#[CH:24].Cl>CN(C=O)C>[CH2:21]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][N:14]1[CH2:13][C@@H:12]([C:10]2[CH:9]=[CH:8][C:6]3[O:7][C:2]([CH3:18])([CH3:1])[O:3][CH2:4][C:5]=3[CH:11]=2)[O:16][C:15]1=[O:17])[CH2:22][C:23]#[CH:24]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 10933894(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneHCID 113792816-Bromohexylbut-3-ynyl ether

Produkt 1

HCID 42625666(5R)-3-[6-(But-3-ynyloxy)hexyl]5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (10 g) in DMF (100 ml) was added dropwise to a stirred suspension of sodium hydride (60% oil dispersion, 2.33 g) in DMF (50 ml) with stirring under nitrogen and maintaining the internal temperature at 0° C. Stirring was continued at 0-5° C. for 1 h. The mixture was recooled to 0° C. and a solution of 6-bromohexyl but-3-ynyl ether (14.7 g) in DMF (50 ml) was added over 1 min. The mixture was then stirred at 20-30° C. for 2 h. 2M HCl (9 ml) was added and the mixture was partitioned between water and diethyl ether. The aqueous layer was extracted with more diethyl ether and the combined organic layers were washed twice with brine. After drying (MgSO4) the solution was concentrated and loaded onto a column of silica gel (600 g) set up in diethyl ether: petroleum ether (bp 40-60° C.) (1:2). The column was eluted successively with this mixture, then (1:1) and then diethyl ether to give the title compound (13.88 g) LCMS RT=3.45 min.

Aufarbeitung

  1. stirringStirring
  2. customwas recooled to 0° C.
  3. stirringThe mixture was then stirred at 20-30° C. for 2 h
  4. customthe mixture was partitioned between water and diethyl ether
  5. extractionThe aqueous layer was extracted with more diethyl ether
  6. washthe combined organic layers were washed twice with brine
  7. dry with materialAfter drying (MgSO4) the solution
  8. concentrationwas concentrated
  9. washThe column was eluted successively with this mixture

Quellen und Nachweise

ORD-Eintrag
ord-7f19a534b9e34c4da7638c8532b05fcc
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405206B2

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