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

HRID 523889Notes

Reaction equation

HRID 523889 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 rt 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-e587fcfca3ce4c5a8ed0911c68474460
Source dataset
uspto-grants-2016_05
Patent number
US09340503B2

Reaction notes

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