Hexamethylphosphoramide → (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-(2-bromo-1-phenylethoxy)-azetidin-2-one

HRID 1075649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1075649
[C:1]1([CH2:7][CH2:8][C:9]([NH:11][C@H:12]([C:20]([NH:22][C@H:23]2[C@@H:26]([O:27][CH:28]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:29]OS(C3C=CC(C)=CC=3)(=O)=O)[NH:25][C:24]2=[O:47])=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-:48].[Li+].CN(P(N(C)C)(N(C)C)=O)C>C(OCC)(=O)C>[C:1]1([CH2:7][CH2:8][C:9]([NH:11][C@H:12]([C:20]([NH:22][C@H:23]2[C@@H:26]([O:27][CH:28]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:29][Br:48])[NH:25][C:24]2=[O:47])=[O:21])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 12679HexamethylphosphoramideHCID 82050Lithium BromideHCID 86754072(3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-{2-(p-toluenesulfonyl)oxy-1-phenylethoxy}-azetidin-2-one

Produkt 1

HCID 70094414(3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-(2-bromo-1-phenylethoxy)-azetidin-2-oneAusbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-{2-(p-toluenesulfonyl)oxy-1 -phenylethoxy}azetidin-2-one (160 mg, 0.244 mmol), lithium bromide (133 mg, 1.525 mmol) and HMPA (4 ml) was stirred at 60° C. for 1.5 hrs. The resulting mixture was diluted with ethyl acetate, washed with water, brine, and dried over sodium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography using hexane-ethyl acetate (1:2) as eluent and 100 mg (3S,4R)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-(2-bromo-1-phenylethoxy)-azetidin-2-one as white foam was obtained in 72% yield.

Aufarbeitung

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. customAfter removal of solvent
  4. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-27a8347654fe4b9f95aa9f28432ca335
Quelldatensatz
uspto-grants-1999_05
Patentnummer
US05905076

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