Hydroxylamine → 7,7-Di-pyridin-2-yl-hept-6-enoic acid hydroxyamide

HRID 404133Notes

Reaction equation

HRID 404133 reaction equation
[OH:1][NH2:2].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](O)=[O:16].CCOC(C)=O>CN(C=O)C.C1COCC1.[Cl-].[Na+].O>[OH:1][NH:2][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=[C:9]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1

Participants

7

Reactant 3

HCID 787HydroxylamineHCID 8857Ethyl AcetateHCID 585450627,7-Di-pyridin-2-yl-hept-6-enoic acid

Product 1

HCID 468523047,7-Di-pyridin-2-yl-hept-6-enoic acid hydroxyamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

HONH2 (50% aqueous, 0.3 mL) was added to IV (32 mg, 0.1 mmol) in DMF (0.3 mL) and THF (0.3 mL) at 0° C. The reaction mixture was stirred at it for 17 h, after which 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 then combined, dried over MgSO4, filtered, and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using CH2Cl2/MeOH (100:3 to 100:10) as eluant to furnish V, 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. customsubsequently evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography
  7. customto furnish V

Sources & evidence

ORD record
ord-3c2a8810ba2f4e9ea9b6eee5b715666b
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

Loading…