L-Tyrosine 1,1-dimethylethyl ester → tert-butyl (2S)-2-[[4-(dihexylamino)-1,1-dioxo-1,2,5-thiadiazol-3-yl]amino]-3-(4-hydroxyphenyl)propanoate

HRID 18051

Reaktionsgleichung

Reaktionsgleichung von HRID 18051
[CH2:1]([N:7]([C:14]1[C:15](OCC)=[N:16][S:17](=[O:20])(=[O:19])[N:18]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:24]([O:28][C:29](=[O:40])[C@H:30]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[NH2:31])([CH3:27])([CH3:26])[CH3:25]>CCO>[C:24]([O:28][C:29](=[O:40])[C@H:30]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[NH:31][C:15]1[C:14]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[N:18][S:17](=[O:19])(=[O:20])[N:16]=1)([CH3:27])([CH3:25])[CH3:26]

Komponenten

4

Edukt 2

HCID 6950582L-Tyrosine 1,1-dimethylethyl esterHCID 221387874-(N,N-di-n-hexylamino)-3-ethoxy-1,1-dioxo-1,2,5-thiadiazole

Produkt 1

HCID 178444783tert-butyl (2S)-2-[[4-(dihexylamino)-1,1-dioxo-1,2,5-thiadiazol-3-yl]amino]-3-(4-hydroxyphenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 4-(N,N-di-n-hexylamino)-3-ethoxy-1,1-dioxo-1,2,5-thiadiazole (400 mg, 1.02 mmol) and L-tyrosine t-butyl ester (261 mg, 1.1 mmol) in EtOH (10 mL) was stirred at room temperature for 36 hrs. The solvent was removed under reduced pressure residue purified by flash column chromatography (silica, hexane:EtOAc 3:1 then 1:1) to give the title compound as a white waxy solid (400 mg, 73%).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure residue
  2. custompurified by flash column chromatography (silica, hexane:EtOAc 3:1

Quellen und Nachweise

ORD-Eintrag
ord-5e7f5be6d76b4fc89846ba27d66b7eec
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741328B2

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