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

HRID 1072470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072470
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-b2ba0f691687446c84233d8b9f627474
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911439B2

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