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

HRID 29358Notes

Reaction equation

HRID 29358 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:17](O)=[O:18].C(Cl)(=O)C(Cl)=O.[CH3:26][O:27][C:28](=[O:50])[C@@H:29]([NH:33][S:34]([C:37]1[CH:42]=[CH:41][C:40]([C:43]2[CH:48]=[CH:47][C:46]([NH2:49])=[CH:45][CH:44]=2)=[CH:39][CH:38]=1)(=[O:36])=[O:35])[CH:30]([CH3:32])[CH3:31]>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:26][O:27][C:28](=[O:50])[C@@H:29]([NH:33][S:34]([C:37]1[CH:42]=[CH:41][C:40]([C:43]2[CH:44]=[CH:45][C:46]([NH:49][C:17]([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]=[CH:13][CH:12]=5)[C:6]=4[C:2]=3[CH3:1])=[O:18])=[CH:47][CH:48]=2)=[CH:39][CH:38]=1)(=[O:36])=[O:35])[CH:30]([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 59847687(S)-2-(4'-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl esterHCID 687163423-Methyl-4-phenyl-benzofuran-2-carboxylic acid

Product 1

HCID 68717097(S)-3-methyl-2-{4'-[(3-methyl-4-phenyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-butyric acid methyl esterYield 29%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To 60 mg (0.24 mmol) 3-methyl-4-phenyl-benzofuran-2-carboxylic acid was added 1 mL of oxalyl chloride and the mixture was refluxed for 1 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 129 mg (0.36 mmol) of (S)-2-(4′-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl ester, 87 mg (0.714 mmol) of 4-(dimethylamino)pyridine and 2 mL of 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 (29% yield) of (S)-3-methyl-2-{4′-[(3-methyl-4-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-ade577c3833146418a468b39c9ba6048
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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