O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 67362073, compound

HRID 1183191Notes

Reaction equation

HRID 1183191 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[C:3](=[O:21])[CH2:4][O:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[N:9]=[C:8]([C:18]([OH:20])=O)[CH:7]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[NH2:46][C@H:47]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[CH3:58])[CH2:48][C:49]([OH:51])=[O:50]>CN(C=O)C>[CH3:23][C:2]([CH3:22])([CH3:1])[C:3](=[O:21])[CH2:4][O:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[N:9]=[C:8]([C:18]([NH:46][C@H:47]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[CH3:58])[CH2:48][C:49]([OH:51])=[O:50])=[O:20])[CH:7]=1

Participants

5

Reactant 3

HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6934180(3S)-3-Amino-3-(2-methylphenyl)propanoic acidHCID 67363376HCID 67363376, compound

Product 1

HCID 67362073HCID 67362073, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

324 mg (0.675 mmol) of 5-(3,3-dimethyl-2-oxo-butoxy)-1-(2-fluoro-phenyl)-1H-pyrazole-3-carboxylic acid were dissolved in 5 ml of DMF and 0.675 mmol of TOTU and 1.35 mmol of EDIA were added. The mixture was stirred for 5 min at room temperature, then 0.675 mmol of (S)-3-amino-3-(2-methyl-phenyl)-propionic acid were added and the mixture was stirred overnight at room temperature. After evaporation of the solvent, the residue was subjected to preparative HPLC to give the title compound in a yield of 67%.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-1f1fb119280b42b3bd23daf6072825b4
Source dataset
uspto-grants-2014_03
Patent number
US08664257B2

Reaction notes

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