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

HRID 1825881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1825881
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-1b158d3c741a4a879b52f7d4bbe40077
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07049306B2

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