Sodium Hydroxide → HCID 71073742, compound

HRID 2361119Notes

Reaction equation

HRID 2361119 reaction equation
[CH3:1][C:2]1[CH2:6][C:5](=[O:7])[N:4]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[N:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[O:42][C:43](=[O:56])[C@H:44]([OH:55])[C@H:45]([NH2:54])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=1[Cl:53].CCN(C(C)C)C(C)C.[OH-].[Na+]>CN(C=O)C.C1COCC1>[Cl:53][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=1[CH2:46][C@@H:45]([NH:54][C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([N:4]2[C:5](=[O:7])[CH2:6][C:2]([CH3:1])=[N:3]2)=[CH:16][CH:15]=1)[C@@H:44]([OH:55])[C:43]([OH:56])=[O:42]

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 1090294-(3-Methyl-5-oxo-2-pyrazolin-1-yl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71073768HCID 71073768, compound

Product 1

HCID 71073742HCID 71073742, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

4-(3-Methyl-5-oxo-2-pyrazolin-1-yl)benzoic acid (42 mg, 0.2 mmol, 1.0 eq.) was combined with DMF (500 μL) and HATU (88 mg, 0.2 mmol, 1.2 eq.) and stirred at room temperature for 15 minutes. (2R,3R)-3-Amino-4-(2-chloro-phenyl)-2-hydroxy-butyric acid methyl ester (47 mg, 0.2 mmol, 1.0 eq.) in DIPEA (70 μL, 2.0 eq.) and DMF (500 μL) was then added and the resulting mixture was stirred overnight at room temperature. THF (500 μL) and 2 M aqueous NaOH (600 μL, 1 mmol) was added and the mixture was heated at 50° C. overnight. The solvent was removed and the product was dissolved in AcOH/H2O (50%) and purified by preparative HPLC to yield the title compound (58.3 mg, 56% purity). MS m/z [M+H]+ calc'd for C21H20ClN3O5, 430.11. found 430.0.

Workup

  1. stirringthe resulting mixture was stirred overnight at room temperature
  2. temperaturethe mixture was heated at 50° C. overnight
  3. customThe solvent was removed
  4. dissolutionthe product was dissolved in AcOH/H2O (50%)
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-70c9d7d76dcb48ffb6dc65e8868eb778
Source dataset
uspto-grants-2014_04
Patent number
US08686184B2

Reaction notes

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