Sodium Bicarbonate → (4-{[(2R)-2-(4-fluorophenyl)propanoyl]amino}phenyl)boronic acid

HRID 1051870Notes

Reaction equation

HRID 1051870 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].[F:17][C:18]1[CH:23]=[CH:22][C:21]([C@@H:24]([CH3:28])[C:25](O)=[O:26])=[CH:20][CH:19]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[F:17][C:18]1[CH:19]=[CH:20][C:21]([C@@H:24]([CH3:28])[C:25]([NH:2][C:3]2[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=2)=[O:26])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 2734614(4-Aminophenyl)boronic acid hydrochlorideHCID 7005040(2R)-2-(4-fluorophenyl)propanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 89924129(4-{[(2R)-2-(4-fluorophenyl)propanoyl]amino}phenyl)boronic acidYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (4-aminophenyl)boronic acid hydrochloride (2.00 g) in DMF (42 mL) was added sodium bicarbonate (2.9 g), (2R)-2-(4-fluorophenyl)propanoic acid (2.04 g) and HATU (6.58 g). The mixture was stirred at room temperature for 72 h. Water (140 mL) was added, and the mixture was stirred for 2 h. The white precipitate was collected by filtration and was washed with water and was dried in vacuum to give 2.86 g of the title compound.

Workup

  1. stirringthe mixture was stirred for 2 h
  2. filtrationThe white precipitate was collected by filtration
  3. washwas washed with water
  4. customwas dried in vacuum

Sources & evidence

ORD record
ord-3c4d16d07284443ab86e0b36e9e9223f
Source dataset
uspto-grants-2016_07
Patent number
US09388177B2

Reaction notes

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