Hydroxyamine hydrochloride → Tert-butyl 1-(3-((hydroxyimino)methyl)phenyl)ethylcarbamate

HRID 467505ノート

反応式

HRID 467505 の反応式
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH:6]=[CH:7][CH:8]=1)=O.C([O-])(=O)C.[Na+].Cl.[NH2:25][OH:26]>C1COCC1>[OH:26][N:25]=[CH:1][C:3]1[CH:4]=[C:5]([CH:9]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH:6]=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 72407279tert-butyl N-[1-(3-formylphenyl)ethyl]carbamate

生成物 1

HCID 76686634Tert-butyl 1-(3-((hydroxyimino)methyl)phenyl)ethylcarbamate収率 100.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl N-[1-(3-formylphenyl)ethyl]carbamate (4.0 g, 16.0 mmol) and sodium acetate (3.3 g, 40.1 mmol) in THF (69 mL) at 0° C. was added hydroxylamine hydrochloride (1.4 g, 20.9 mmol). The reaction was allowed to warm to ambient temperature and stirred for 16 hours. The reaction was concentrated in vacuo and the residue partitioned between EtOAc and water and the layers separated. The organic layer was washed with brine (×2), dried (Na2SO4), filtered and concentrated in vacuo to give the sub-title compound as a colourless gel (4.24 g, quantitative Yield). 1H NMR (400 MHz, DMSO) δ 1.30 (d, 3H), 1.33 (d, 9H), 4.61 (dd, 1H), 7.24-7.38 (m, 2H), 7.41 (q, 2H), 7.53 (s, 1H), 8.11 (s, 1H) and 11.20 (s, 1H) ppm; MS (ES+) 265.3.

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue partitioned between EtOAc and water
  3. customthe layers separated
  4. washThe organic layer was washed with brine (×2)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d133307ec5564561b23ce34fd453ab9a
出典データセット
uspto-grants-2014_01
特許番号
US08623869B2

反応ノート

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