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

HRID 325212Notes

Reaction equation

HRID 325212 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-edb12822ec9f482bb59fa36e2a1010e4
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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