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

HRID 29362Notes

Reaction equation

HRID 29362 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:20](O)=[O:21].C(Cl)(=O)C(Cl)=O.CN(C=O)C.[CH3:34][O:35][C:36](=[O:58])[C@@H:37]([NH:41][S:42]([C:45]1[CH:50]=[CH:49][C:48]([C:51]2[CH:56]=[CH:55][C:54]([NH2:57])=[CH:53][CH:52]=2)=[CH:47][CH:46]=1)(=[O:44])=[O:43])[CH:38]([CH3:40])[CH3:39]>N1C=CC=CC=1>[CH3:34][O:35][C:36](=[O:58])[C@@H:37]([NH:41][S:42]([C:45]1[CH:50]=[CH:49][C:48]([C:51]2[CH:52]=[CH:53][C:54]([NH:57][C:20]([C:3]3[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[C:7]([C:11]5[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=5)[C:6]=4[C:2]=3[CH3:1])=[O:21])=[CH:55][CH:56]=2)=[CH:47][CH:46]=1)(=[O:44])=[O:43])[CH:38]([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 59847687(S)-2-(4'-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl esterHCID 687100553-Methyl-4-(3-nitro-phenyl)-benzofuran-2-carboxylic acid

Product 1

HCID 68714534(S)-3-methyl-2-(4'-{[3-methyl-4-(3-nitro-phenyl)-benzofuran-2-carbonyl]-amino}-biphenyl-4-sulfonylamino)-butyric acid methyl esterYield 18.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 100 mg (0.34 mmol) of 3-methyl-4-(3-nitro-phenyl)-benzofuran-2-carboxylic acid was added 2 mL of oxalyl chloride and the resulting mixture was refluxed for 2 h in the presence of a catalytic amount of DMF, then the excess oxalyl chloride was removed under vacuum. The residue was dissolved in 1 mL of dichloromethane and was added to a mixture of 183 mg (0.5 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 41 mg of (S)-3-methyl-2-(4′-{[3-methyl-4-(3-nitro-phenyl)-benzofuran-2-carbonyl]-amino}-biphenyl-4-sulfonylamino)-butyric acid methyl ester as white solid.

Workup

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

Sources & evidence

ORD record
ord-981587b49ea8469f94c72ed2be7b5754
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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