Triethylamine → Methyl cis-1-(2,4-Dimethoxybenzyl)-3-phenoxyacetamido-4-oxo-2-azetidinecarboxylate

HRID 1974177

Reaktionsgleichung

Reaktionsgleichung von HRID 1974177
[N:1]([C@H:4]1[C:7](=[O:8])[N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[C@H:5]1[C:20]([O:22][CH3:23])=[O:21])=[N+]=[N-].[H][H].C(N(CC)CC)C.[O:33]([CH2:40][C:41](Cl)=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>[Pd].C(Cl)Cl.CCOCC.C(O)C>[CH3:19][O:18][C:11]1[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=1[CH2:9][N:6]1[C:7](=[O:8])[C@H:4]([NH:1][C:41](=[O:42])[CH2:40][O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@H:5]1[C:20]([O:22][CH3:23])=[O:21]

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 69703Phenoxyacetyl chlorideHCID 86734328Methyl cis-1-(2,4-dimethoxybenzyl)-3-azido-4-oxoazetidine-2-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 70577439Methyl cis-1-(2,4-Dimethoxybenzyl)-3-phenoxyacetamido-4-oxo-2-azetidinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture containing 10.0 g (0.0312 mole) of methyl cis-3-azido-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate, 1.0 g of 10% palladium on carbon and 200 ml of ethanol was hydrogenated at 60 psi of hydrogen at 40°-45° for 2 hours. The reaction mixture was allowed to cool to 25° and was filtered through celite. After removing the solvents in vacuo there remained a clear, yellow gum. The crude amine was taken up in 100 ml of anhydrous methylene dichloride and was cooled to 0° in an ice bath. To this solution was added 4.32 ml (0.0312 mole) of triethylamine followed by the slow addition of a solution of 5.32 g (0.0312 mole) of phenoxyacetyl chloride in 40 ml of methylene dichloride. The mixture was stirred at 0° for 1 hour then extracted successively with water, aqueous hydrochloric acid, aqueous sodium bicarbonate and brine and was dried over anhydrous magnesium sulfate. Filtration followed by removal of the solvent in vacuo afforded a yellow solid. This material was partially dissolved in ether, cooled to -25° and filtered to give methyl cis-1-(2,4-dimethoxybenzyl)-4-oxo-3-phenoxyacetylaminoazetidine-2-carboxylate as a white solid; tlc: benzene:ethyl acetate (1:1), silica gel, Rf = 0.38; mp 115.5°-116.0° (ethyl acetate-hexane).

Aufarbeitung

  1. temperatureto cool to 25°
  2. filtrationwas filtered through celite
  3. customAfter removing the solvents in vacuo
  4. temperaturewas cooled to 0° in an ice bath
  5. extractionthen extracted successively with water, aqueous hydrochloric acid, aqueous sodium bicarbonate and brine
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. filtrationFiltration
  8. customfollowed by removal of the solvent in vacuo
  9. customafforded a yellow solid
  10. temperaturecooled to -25°
  11. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-66b1fb741ea14e949064ecebeed1fab1
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US04000154

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