Iodoethane → HCID 12515028, Verbindung

HRID 342715

Reaktionsgleichung

Reaktionsgleichung von HRID 342715
COCCCCCCCCCCC[C:14]([NH:16][C@@H:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:18])=[O:15].[C:24]([O:28]C(N[C@@H](C(O)=O)C)=O)([CH3:27])([CH3:26])[CH3:25].O.O.O.O.O.[OH-].C[N+](C)(C)C.C(I)C>C(#N)C>[C:24]([O:28][C:14]([NH:16][C@@H:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:18])=[O:15])([CH3:27])([CH3:26])[CH3:25]

Komponenten

6

Edukt 4

HCID 6340IodoethaneHCID 82620Tetramethylammonium Hydroxide PentahydrateHCID 637606BOC-D-alanineHCID 15870267HCID 15870267, Verbindung

Produkt 1

HCID 12515028HCID 12515028, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Reaction Scheme 6 illustratively shows the preparation of N-(12-methoxy-1-oxododecyl)-D-alanine, ethyl ester wherein N-(t-butyloxycarbonyl)-D-alanine (16) is treated with tetramethylammonium hydroxide pentahydrate in acetonitrile followed by the addition of ethyl iodide to form N-(t-butyloxycarbonyl)-D-alanine, ethyl ester (17) which in turn reacts with trifluoroacetic acid in methylene chloride to give the trifluoroacetate salt of D-alanine ethyl ester (18) which, when treated with 2-methoxydodecanoyl chloride (9) in methylene chloride, gives the desired fatty acid amino ester (19).

Aufarbeitung

  1. customReaction Scheme 6

Quellen und Nachweise

ORD-Eintrag
ord-c9943100722e477b81ddb31f495ec7d2
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859052

Verknüpfte Notizen

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