2-Phenylisobutyric acid → HCID 22026295, compound

HRID 1793237Notes

Reaction equation

HRID 1793237 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=O.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH3:46][O:47][C:48]1[CH:49]=[C:50]([CH:53]=[CH:54][C:55]=1[O:56][CH3:57])[CH2:51][NH2:52]>CN(C=O)C.CCOC(C)=O>[CH3:46][O:47][C:48]1[CH:49]=[C:50]([CH:53]=[CH:54][C:55]=1[O:56][CH3:57])[CH2:51][NH:52][C:3](=[O:5])[C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:1])[CH3:6]

Participants

7

Reactant 4

HCID 132222-Phenylisobutyric acidHCID 79832VeratrylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 22026295HCID 22026295, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methyl-2-phenylpropionic acid (3.28 g, 20 mmol) in DMF (50 ml) was treated sequentially with N,N-diisopropylethylamine (8.09 g, 80 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (7.60 g, 20 mmol) then 3,4-dimethoxybenzylamine (3.34 g, 20 mmol) and then stirred at room temperature, under argon for 24 h. The reaction mixture was diluted with EtOAc then washed with water (3×) then brine. The organic phase was dried (MgSO4) and the solvent removed in vacuo. The residue was triturated with diethyl ether/pentane to afford the title compound as a beige solid (5.95 g, 95%).

Workup

  1. washthen washed with water (3×)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customthe solvent removed in vacuo
  4. customThe residue was triturated with diethyl ether/pentane

Sources & evidence

ORD record
ord-26e67c3358a347cdbaf3b4613a22bfa4
Source dataset
uspto-grants-2006_07
Patent number
US07078565B2

Reaction notes

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