O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate → HCID 67364070, compound

HRID 1183180Notes

Reaction equation

HRID 1183180 reaction equation
[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]1[C:34]([O:35][C:36]([N:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)=[O:37])=[CH:33][C:32]([C:43]([OH:45])=O)=[N:31]1.[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]>>[C:49]([CH2:48][C@H:47]([NH:46][C:43]([C:32]1[CH:33]=[C:34]([O:35][C:36]([N:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)=[O:37])[N:30]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[F:23])[N:31]=1)=[O:45])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[CH3:58])([OH:51])=[O:50]

Participants

4

Reactant 3

HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 6934180(3S)-3-Amino-3-(2-methylphenyl)propanoic acidHCID 67363573HCID 67363573, compound

Product 1

HCID 67364070HCID 67364070, compoundYield 67%

Procedure

0.675 mmol of TOTU and 1.35 mmol of EDIA were added to the filtrate containing 1-(2-fluoro-phenyl)-5-(pyrrolidine-1-carbonyloxy)-1H-pyrazole-3-carboxylic acid obtained in step 1. The mixture was stirred for 5 min at room temperature, and then 0.675 mmol of (S)-3-amino-3-(2-methyl-phenyl)-propionic acid were added and the mixture was stirred overnight at RT. Then the solvent was evaporated and the residue subjected to preparative HPLC to give the title compound in a yield of 67%.

Workup

  1. stirringthe mixture was stirred overnight at RT
  2. customThen the solvent was evaporated

Sources & evidence

ORD record
ord-5323397b752e4dfd976f0c2838eb6f2e
Source dataset
uspto-grants-2014_03
Patent number
US08664257B2

Reaction notes

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