L-Tyrosine 1,1-dimethylethyl ester → N-(4-ethoxy-1-oxo-1,2,5-thiadiazol-3-yl)-L-tyrosine tert-butyl ester

HRID 2225034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2225034
C(O[C:4]1[C:8]([O:9][CH2:10][CH3:11])=[N:7][S:6](=[O:12])[N:5]=1)C.[C:13]([O:17][C:18](=[O:29])[C@H:19]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[NH2:20])([CH3:16])([CH3:15])[CH3:14]>C(O)C>[C:13]([O:17][C:18](=[O:29])[C@H:19]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[NH:20][C:4]1[C:8]([O:9][CH2:10][CH3:11])=[N:7][S:6](=[O:12])[N:5]=1)([CH3:16])([CH3:14])[CH3:15]

Komponenten

4

Edukt 2

HCID 6950582L-Tyrosine 1,1-dimethylethyl esterHCID 12927269Diethoxy-1,2,5-thiadiazol-1-one

Produkt 1

HCID 53908618N-(4-ethoxy-1-oxo-1,2,5-thiadiazol-3-yl)-L-tyrosine tert-butyl esterAusbeute 882,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 3,4-diethoxy-1-oxo-1,2,5-thiadiazole (1 g, 0.52 mmol) and L-tyrosine t-butyl ester (1.25 g, 0.52 mmol) in ethanol (25 mL) was stirred at room temperature for 60 hr. Solvent was removed under reduced pressure and the residue purified by flash column chromatography (silica, hexane:EtOAc 1:1 to give the title intermediate (1.75 g, 88%).

Aufarbeitung

  1. customSolvent was removed under reduced pressure
  2. customthe residue purified by flash column chromatography (silica, hexane:EtOAc 1:1

Quellen und Nachweise

ORD-Eintrag
ord-cd095fca41ee41b29fc8f2ef5a9532ae
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07378529B2

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