Thiophenol → 4-(2-Pyridylthio)-2-phenyl benzoyl methionine methyl ester

HRID 2121118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2121118
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.Br[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[H-].[Na+].[C:18]([O-:21])([O-])=O.[K+].[K+].[CH3:24][O:25][C:26](=[O:33])[C@H:27]([CH2:29][CH2:30][S:31][CH3:32])[NH2:28]>CN(C=O)C.N1C=CC=CC=1>[CH3:24][O:25][C:26](=[O:33])[C@H:27]([CH2:29][CH2:30][S:31][CH3:32])[NH:28][C:18](=[O:21])[C:4]1[CH:5]=[CH:6][C:1]([S:7][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:2][C:3]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

8

Edukt 5

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 64684methyl (2S)-2-amino-4-(methylsulfanyl)butanoateHCID 234362812-Bromopyridine hydrobromide

Produkt 1

HCID 206227894-(2-Pyridylthio)-2-phenyl benzoyl methionine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of the resultant thiophenol from Example 12A (1.0 equivalent) is treated with 2-bromopyridine hydrobromide (1.0 equivalent) in the presence of a NaH (2.0 equivalents), or K2CO3 (3.0 equivalents) in DMF or pyridine. The product is isolated by removal of the solvent and chromatography on silica gel. The resultant ester is hydrolyzed according to the procedure of Example 6C and then is coupled to methionine methyl ester according to the procedure of Example 1C to give the title compound.

Aufarbeitung

  1. customThe product is isolated by removal of the solvent and chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-eedddb4541fc469794bc9b75ff40958c
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693123B2

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