Pyridine → (S)-2-{4'-[(3-methyl-4-propoxy-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester

HRID 29350Notes

Reaction equation

HRID 29350 reaction equation
[CH2:1]([O:3][C:4]1[C:9]2[C:10]([CH3:16])=[C:11]([C:13]([OH:15])=O)[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:2].[CH3:17]N(C=O)C.[CH3:22][O:23][C:24](=[O:46])[C@@H:25]([NH:29][S:30]([C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=2)=[CH:35][CH:34]=1)(=[O:32])=[O:31])[CH:26]([CH3:28])[CH3:27].N1C=CC=CC=1>C(Cl)(=O)C(Cl)=O>[CH3:22][O:23][C:24](=[O:46])[C@@H:25]([NH:29][S:30]([C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:40]=[CH:41][C:42]([NH:45][C:13]([C:11]3[O:12][C:8]4[CH:7]=[CH:6][CH:5]=[C:4]([O:3][CH2:1][CH2:2][CH3:17])[C:9]=4[C:10]=3[CH3:16])=[O:15])=[CH:43][CH:44]=2)=[CH:35][CH:34]=1)(=[O:32])=[O:31])[CH:26]([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 59847687(S)-2-(4'-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl esterHCID 687136834-Ethoxy-3-methyl-benzofuran-2-carboxylic acid

Product 1

HCID 68709957(S)-2-{4'-[(3-methyl-4-propoxy-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl esterYield 57%

Reagents, catalysts & solvents 1

HCID 65578Oxalyl chlorideSolvent

Procedure

A solution of 110 mg (0.47 mmol) of 4-ethoxy-3-methyl-benzofuran-2-carboxylic acid in 4 mL of oxalyl chloride was refluxed for 4 h in the presence of a catalytic amount of DMF. The excess oxalyl chloride was then removed under vacuum. The residue was dissolved in 2 mL of dichloromethane and was added to a mixture of 204 mg (0.56 mmol) of (S)-2-(4′-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl ester, and 2 mL of pyridine in an ice/water bath. The mixture was stirred at room temperature overnight. All the solvents were removed under vacuum. Column chromatography on silica gel gave 152 mg (57% yield) of (S)-2-{4′-[(3-methyl-4-propoxy-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester as a white solid.

Workup

  1. customThe excess oxalyl chloride was then removed under vacuum
  2. dissolutionThe residue was dissolved in 2 mL of dichloromethane
  3. customAll the solvents were removed under vacuum

Sources & evidence

ORD record
ord-8ccb7c25c07445a988b502f3e7844350
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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