Imidazole → HCID 87884639, Verbindung

HRID 891668

Reaktionsgleichung

Reaktionsgleichung von HRID 891668
[CH3:1][O:2][C:3](=[O:18])[C@H:4]([CH2:16][OH:17])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[Si:19](Cl)([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C=CN=C1.CN(C)C=[O:45]>>[CH3:1][O:2][C:3](=[O:18])[C@H:4]([CH2:16][OH:17])[N:5]([O:45][Si:19]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Komponenten

5

Edukt 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 6999535N-((Phenylmethoxy)carbonyl)-L-serine methyl ester

Produkt 1

HCID 87884639HCID 87884639, VerbindungAusbeute 99 %

Versuchsvorschrift

Subsequently, to a solution of N-carbobenzyloxy-L-serine methyl ester (4.40 g, 16.7 mmol) in dimethylformamide (210 ml) were added t-butyldiphenylsilyl chloride (5.20 ml, 20.0 mmol) and imidazole (1.36 g, 20.0 mmol) in an ice bath, and the mixture was stirred at room temperature for 3 days. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (8:1→6:1) as the eluant to afford t-butyldiphenylsilyloxy-N-carbobenzyloxy-L-serine methyl ester (18.8 g, 99%).

Aufarbeitung

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
  3. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-69b9594d73504a47a2463d692ed1ecbb
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001897B2

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