Imidazole → HCID 67797177, Verbindung

HRID 1196198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1196198
[OH:1][CH2:2][C:3]([C@H:5]1[N:8]([CH:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:7](=[O:28])[C@@H:6]1[C@H:29]([O:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH3:30])=[CH2:4].N1C=CN=C1.[C:47]([Si:51]([CH3:54])([CH3:53])Cl)([CH3:50])([CH3:49])[CH3:48]>CN(C)C=O.O.C(OCC)(=O)C>[Si:51]([O:1][CH2:2][C:3]([C@H:5]1[N:8]([CH:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[C:7](=[O:28])[C@@H:6]1[C@H:29]([O:31][C:32]([O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:33])[CH3:30])=[CH2:4])([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:54])[CH3:53]

Komponenten

7

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67796345HCID 67796345, Verbindung

Produkt 1

HCID 67797177HCID 67797177, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of (3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone (20 g) and imidazole (5.6 g) in dry dimethylformamide (45 ml) was treated with t-butyl dimethyl chlorosilane (6.77 g) at room temperature for 2 hours. The reaction mixture was diluted with cold water (200 ml) and ethyl acetate (150 ml). The aqueous layer was extracted with ethyl acetate (150 ml). The combined extracts were washed successively with 5% hydrochloric acid solution (80 ml×2) and brine (80 ml), and dried over anhydrous sodium sulfate. After filtration and concentration of the filtrate in vacuo, the concentrate was crystallized from isopropanol to give crystals of (3S,4S)-4-(1-t-butyldimethylsilyloxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone. m.p., 90°-92° C.

Aufarbeitung

  1. extractionThe aqueous layer was extracted with ethyl acetate (150 ml)
  2. washThe combined extracts were washed successively with 5% hydrochloric acid solution (80 ml×2) and brine (80 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration and concentration of the filtrate in vacuo
  5. customthe concentrate was crystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-bb8a0035639f4e20aabd2db56c6e8941
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112966

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