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Acetone → 2,2,2-Trichloroethyl 3-azido-3-methyl-7-(2-phenylacetamido)cepham-4-carboxylate

HRID 1438794
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1438794
Br[CH2:2][CH2:3][C:4]1(C)[CH:8]([C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10])[N:7]2[C:17](=[O:29])[CH:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@H:6]2[S:5]1.[N-:31]=[N+:32]=[N-:33].[Na+].CC(C)=O>O>[N:31]([C:3]1([CH3:2])[CH:8]([C:9]([O:11][CH2:12][C:13]([Cl:15])([Cl:14])[Cl:16])=[O:10])[N:7]2[C:17](=[O:29])[CH:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C@H:6]2[S:5][CH2:4]1)=[N+:32]=[N-:33]
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Komponenten

5

Edukt 3

HCID 180AcetoneHCID 33557Sodium AzideHCID 705961582,2,2-Trichloroethyl 2-bromoethyl-2-methyl-6-(2-phenyl-acetamido)penam-3-carboxylate

Produkt 1

HCID 867333872,2,2-Trichloroethyl 3-azido-3-methyl-7-(2-phenylacetamido)cepham-4-carboxylateAusbeute 17,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

A mixture of 2,2,2-trichloroethyl 2-bromoethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (1.08 g), sodium azide (0.26 g), acetone (20 ml) and water (4 ml) was stirred for 4 hours at room temperature. After acetone was distilled off under reduced pressure, the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with water, with saturated sodium bicarbonate aqueous solution and further with water and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure and a small quantity of ether was added to the residue to give colorless crystals of 2,2,2,-trichloroethyl 3-azido-3-methyl-7-(2-phenylacetamido)cepham-4-carboxylate (170 mg). This substance was recrystallized from carbon tetrachloride to give crystals melting at 136° to 140° C.

Aufarbeitung

  1. distillationAfter acetone was distilled off under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water, with saturated sodium bicarbonate aqueous solution and further with water
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. additiona small quantity of ether was added to the residue

Quellen und Nachweise

ORD-Eintrag
ord-b38d225e193446e0974e3114040d8dea
Quelldatensatz
uspto-grants-1977_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04056521

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