Dimethylformamide → HCID 68712966, compound

HRID 29342Notes

Reaction equation

HRID 29342 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9]([CH3:15])=[C:10]([C:12]([OH:14])=O)[O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.CN(C=O)C.[CH3:27][O:28][C:29](=[O:51])[C@@H:30]([NH:34][S:35]([C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:49]=[CH:48][C:47]([NH2:50])=[CH:46][CH:45]=2)=[CH:40][CH:39]=1)(=[O:37])=[O:36])[CH:31]([CH3:33])[CH3:32]>N1C=CC=CC=1>[CH3:27][O:28][C:29](=[O:51])[C@@H:30]([NH:34][S:35]([C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:45]=[CH:46][C:47]([NH:50][C:12]([C:10]3[O:11][C:7]4[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=4[C:9]=3[CH3:15])=[O:14])=[CH:48][CH:49]=2)=[CH:40][CH:39]=1)(=[O:37])=[O:36])[CH:31]([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 130446384-Methoxy-3-methylbenzofuran-2-carboxylic acidHCID 59847687(S)-2-(4'-amino-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl ester

Product 1

HCID 68712966HCID 68712966, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 110 mg (0.53 mmol) of 4-methoxy-3-methyl-benzofuran-2-carboxylic acid was added 2 mL of oxalyl chloride and the resulting mixture was refluxed for 4 h in the presence of a catalytic amount of DMF, then the excess oxalyl chloride was removed under vacuum. The residue was dissolved in 2 mL of dichloromethane and was added to a mixture of 232 mg (0.64 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 95 mg (33% yield) of (S)-2-{4′-[(4-methoxy-3-methyl-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester as off white solid.

Workup

  1. customthe excess oxalyl chloride was 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-2f774a8eda2548d288162e39266d9e33
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

Loading…