Citric Acid → 3-{(2R)-2-[(3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl]propionyl}-N-cyclohexyl-p-toluenesulfonamide

HRID 1250997

Reaktionsgleichung

Reaktionsgleichung von HRID 1250997
[CH:1]1([N:7]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])C(=O)CC)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Mg]Cl)(CC)C.C(O[C@H:32]1[NH:35][C:34](=[O:36])[C@@H:33]1[C@H:37]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH3:38])(=O)C.[C:47](O)(=O)[CH2:48][C:49](CC(O)=O)(C(O)=O)[OH:50]>O1CCCC1.C(OCC)(=O)C>[Si:40]([O:39][C@@H:37]([C@@H:33]1[C@@H:32]([C@@H:48]([CH3:47])[C:49]([C:20]2[CH:19]=[C:18]([CH3:21])[CH:17]=[CH:16][C:15]=2[S:12]([NH:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)(=[O:13])=[O:14])=[O:50])[NH:35][C:34]1=[O:36])[CH3:38])([C:43]([CH3:44])([CH3:45])[CH3:46])([CH3:41])[CH3:42]

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 10935078AzetidonHCID 18325691N-cyclohexyl-N-p-toluenesulfonylpropionamideHCID 178418314HCID 178418314, Verbindung

Produkt 1

HCID 699481593-{(2R)-2-[(3S,4R)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-2-oxoazetidin-4-yl]propionyl}-N-cyclohexyl-p-toluenesulfonamideAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Under a nitrogen atmosphere, 309 mg (1.0 mmol) of N-cyclohexyl-N-p-toluenesulfonylpropionamide was charged in a 30-ml three-necked flask to dissolve it in 2 ml of tetrahydrofuran. To the resulting solution, 2.2 ml (2.2 mmol) of a tetrahydrofuran solution (0.99M) of sec-butylmagnesium chloride was slowly added dropwise at room temperature. The resulting mixture was reacted for 25 minutes under the same conditions. After cooling to 5° C., 2 ml of a tetrahydrofuran solution of 287 mg (1.0 mmol) of (3R,4R)-4-acetoxy-3-[(R)-1-tert-butyldimethylsilyloxyethyl]azetidin-2-one was added at the same temperature. The resulting mixture was stirred for 10 minutes, added with 10 ml of ethyl acetate and then added dropwise with 2 ml of a 10% aqueous solution of citric acid. After separation, the organic layer was washed with 2 ml of a saturated aqueous solution of sodium bicarbonate and 2 ml of a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by column chromatography, whereby 339 mg of a condensation product was obtained (yield: 63%, β:α=92:8).

Aufarbeitung

  1. customThe resulting mixture was reacted for 25 minutes under the same conditions
  2. customAfter separation
  3. washthe organic layer was washed with 2 ml of a saturated aqueous solution of sodium bicarbonate and 2 ml of a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4036d989b0d04f639287d2bcd0209ed2
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06340751B1

Verknüpfte Notizen

Wird geladen…