3-Bromo-2-methyl-1-propene → N-(tert-butoxycarbonyl)-N-(2-methylprop-2-enyl)glycine tert-butyl ester

HRID 276687

Reaktionsgleichung

Reaktionsgleichung von HRID 276687
[C:1]([O:5][C:6](=[O:16])[CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].Br[CH2:18][C:19]([CH3:21])=[CH2:20]>>[C:1]([O:5][C:6](=[O:16])[CH2:7][N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:20][C:19]([CH3:21])=[CH2:18])([CH3:3])([CH3:4])[CH3:2]

Komponenten

3

Edukt 2

HCID 3577853-Bromo-2-methyl-1-propeneHCID 4097102tert-Butyl ((tert-butoxycarbonyl)amino)acetate

Produkt 1

HCID 18316043N-(tert-butoxycarbonyl)-N-(2-methylprop-2-enyl)glycine tert-butyl ester

Versuchsvorschrift

N-(tert-Butoxycarbonyl)glycine tert-butyl ester was reacted with 3-bromo-2-methylpropene according to Method B8b, Step 1 to give N-(tert-butoxycarbonyl)-N-(2-methylprop-2-enyl)glycine tert-butyl ester. The ester was reduced according to Method B8b, Step 2 to give N-(tert-butoxycarbonyl)-N-(2-hydroxyethyl)-1-amino-2-methylprop-2-ene. The alcohol was treated with p-toluenesulfonyl chloride according to Method B8b, Step 3 to give N-(tert-butoxycarbonyl)-N-(2-tosyloxyethyl)-1-amino-2-methylprop-2-ene. The carbamate was deprotected according to Method B8b, Step 4 to give N-(2-tosyloxyethyl)-2-methylprop-2-en-1-ammonium trifluoroacetate. The tosylate was reacted with 2-methyl-4-nitrophenyl isocyanate according to Method C5a to afford 2-(2-methyl-4-nitrophenylimino)-3-(2methylprop-2-enyl)-1,3-oxazolidine.

Quellen und Nachweise

ORD-Eintrag
ord-e68c8654e23548f68f7c58d6ace0ae87
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06353006B1

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