Hydroxyamine hydrochloride → HCID 86685090, compound

HRID 1750846Notes

Reaction equation

HRID 1750846 reaction equation
[F:1][C:2]1[C:10]2[C:9]([CH3:12])([CH3:11])[O:8][B:7]([OH:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:14]=O.[NH2:16][OH:17].Cl.CC([O-])=O.[Na+]>C1COCC1.O>[F:1][C:2]1[C:10]2[C:9]([CH3:12])([CH3:11])[O:8][B:7]([OH:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:14]=[N:16][OH:17]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86685089HCID 86685089, compound

Product 1

HCID 86685090HCID 86685090, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-fluoro-1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde (136 mg, 0.7 mmol) and NH2OH.HCl (58.5 mg, 0.84 mmol) in THF (4 mL) and H2O (1 mL) at rt was added NaOAc (80.5 mg, 0.98 mmol). The reaction mixture was stirred for 2 h and diluted with H2O. The mixture was extracted three times with ethyl acetate and the organic layer was separated. The organic solution was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give crude compound 4-fluoro-1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-5-carbaldehyde oxime as a light yellow solid. It was used in next step without further purification.

Workup

  1. extractionThe mixture was extracted three times with ethyl acetate
  2. customthe organic layer was separated
  3. washThe organic solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ccf4c3b589914ba2a30ce2c1b8562958
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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