Hydroxylamine → 6-(Di-pyridin-2-yl-amino)-hexanoic acid hydroxyamide

HRID 404136

Reaction equation

HRID 404136 reaction equation
[OH:1][NH2:2].C[O:4][C:5](=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.CCOC(C)=O>CN(C=O)C.C1COCC1.[Cl-].[Na+].O>[OH:1][NH:2][C:5](=[O:4])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

7

Reactant 3

HCID 787HydroxylamineHCID 8857Ethyl AcetateHCID 585450216-(Di-pyridin-2-yl-amino)-hexanoic acid methyl ester

Product 1

HCID 468523056-(Di-pyridin-2-yl-amino)-hexanoic acid hydroxyamideYield 30%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

HONH2 (50% aqueous, 0.3 mL) was added to II (32 mg, 0.1 mmol) in DMF (0.3 mL) and THF (0.3 mL) at 0° C. The reaction mixture was agitated at rt for 17 h. Brine (3 mL) and EtOAc (3 mL) were added, the phases were separated, and the aqueous phase was extracted with EtOAc (2×3 mL). The organic phases were combined, dried over MgSO4, filtered then evaporated under reduced pressure. The residue was purified by silica gel column chromatography with CH2Cl2/MeOH (100:3 to 100:10) to furnish IV as a colourless oil (9.6 mg, 30%).

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with EtOAc (2×3 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthen evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography with CH2Cl2/MeOH (100:3 to 100:10)

Sources & evidence

ORD record
ord-0891a9eda4f543a68f0558d0b160ba11
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Linked notes

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