Hydrochloric Acid → HCID 54369044, Verbindung

HRID 279783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 279783
[C:1]([CH2:3][CH:4]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[O:17][CH3:18])[C:6](=[O:19])[CH2:5]1)#N.ClCCl.[CH2:23]([OH:25])[CH3:24].Cl.CC[O:29]CC>>[CH3:18][O:17][C:10]1[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:9]=1[CH2:8][N:7]1[C:6](=[O:19])[CH2:5][CH:4]1[CH2:3][C:1]([O:25][CH2:23][CH3:24])=[O:29]

Komponenten

6

Edukt 5

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 14456868HCID 14456868, Verbindung

Produkt 1

HCID 54369044HCID 54369044, VerbindungAusbeute 8,2 %

Versuchsvorschrift

To a solution of 5.2 g (20 millimoles) of 4-cyanomethyl-1-(2,4-dimethoxy-benzyl)-2-azetidinone prepared according to the preceding paragraph in 40 ml of anhydrous ether and 40 ml of anhydrous dichloro methane 1.24 ml (21.2 millimoles) of ethanol are added and into the solution gaseous hydrogen chloride developed from 80 ml of concentrated aqueous hydrochloric acid is introduced under stirring and ice-cooling. The mixture is allowed to stand in a refrigerator overnight, the solution is evaporated to dryness and the residue is dissolved in about 25 ml of water. The pH of the aqueous solution is adjusted to 7 by adding a 10% aqueous sodium hydroxide solution and the solution thus obtained is allowed to stand overnight. The mixture becomes blue and the precipitated white crystals are filtered off. The aqueous filtrate is extracted five times with 10 ml of ether each. The united etheral phases are dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated. The residual oil (1 g) is separated by means of preparative thin layer chromatography (adsorbent: Kieselgel PF254+366 ; develop agent: n-heptane-acetone 7:3). Thus 0.501 g of ethyl [1-(2,4-dimethoxy-benzyl)-4-oxo-2-azetidinyl]-acetate is obtained. Yield: 8.2%.

Aufarbeitung

  1. additionis introduced
  2. temperatureice-cooling
  3. customto stand in a refrigerator overnight
  4. customthe solution is evaporated to dryness
  5. dissolutionthe residue is dissolved in about 25 ml of water
  6. additionby adding a 10% aqueous sodium hydroxide solution
  7. customthe solution thus obtained
  8. filtrationthe precipitated white crystals are filtered off
  9. extractionThe aqueous filtrate is extracted five times with 10 ml of ether each
  10. dry with materialThe united etheral phases are dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. customthe filtrate is evaporated
  13. customThe residual oil (1 g) is separated by means of preparative thin layer chromatography (adsorbent: Kieselgel PF254+366 ; develop agent: n-heptane-acetone 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-86d804fb54cc4650bdd0f19841e4b04c
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587049

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