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

HRID 383082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 383082
CO[C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][C:5]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Br.Br[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1.[H-].[Na+].C([O-])([O-])=O.[K+].[K+].[CH3:34][O:35][C:36](=[O:43])[C@H:37]([CH2:39][CH2:40][S:41][CH3:42])[NH2:38]>CN(C=O)C.N1C=CC=CC=1>[CH3:34][O:35][C:36](=[O:43])[C@H:37]([CH2:39][CH2:40][S:41][CH3:42])[NH:38][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([S:10][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:6][C:5]=1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

8

Edukt 5

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 64684methyl (2S)-2-amino-4-(methylsulfanyl)butanoateHCID 234362812-Bromopyridine hydrobromideHCID 543640194-Mercapto-2-phenylbenzoic acid methyl ester

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-007a24b78e9a40b7b6fd9167c76b136d
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310095B1

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