Hydroxyamine hydrochloride → benzyl N-[(2R,3S)-1-[(2,4-dimethoxyphenyl)methyl]-2-[(2E)-2-hydroxyiminoethyl]-4-oxoazetidin-3-yl]carbamate

HRID 708452ノート

反応式

HRID 708452 の反応式
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].[CH3:9][O:10][C:11]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:12]=1[CH2:13][N:14]1[C@H:17]([CH2:18][CH:19]=O)[C@H:16]([NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:15]1=[O:32]>O.CCO>[CH3:9][O:10][C:11]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:12]=1[CH2:13][N:14]1[C:15](=[O:32])[C@@H:16]([NH:21][C:22](=[O:31])[O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@H:17]1[CH2:18]/[CH:19]=[N:2]/[OH:3]

参加物

6

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 131733784Benzyl((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-(2-oxoethyl)azetidin-3-yl)carbamate

生成物 1

HCID 140689339benzyl N-[(2R,3S)-1-[(2,4-dimethoxyphenyl)methyl]-2-[(2E)-2-hydroxyiminoethyl]-4-oxoazetidin-3-yl]carbamate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 962Water溶媒

実験手順

To a solution of hydroxylamine hydrochloride (160 mg, 2.25 mmol) and sodium bicarbonate (2.4 mL, 2.23 mmol) in water (6 mL) was added a solution of benzyl ((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-(2-oxoethyl)azetidin-3-yl)carbamate (886 mg, 2.15 mmol) in EtOH (200 μL) followed by an EtOH (200 μL) wash. After stirring for 20 h, the reaction mixture was partially concentrated in vacuo and partitioned between DCM and brine. The aqueous layer was extracted with DCM (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was used as such in the following step. LCMS: Rt=0.76 min, m/z=428.1 (M+1). Method 2m_acidic.

後処理

  1. washwash
  2. concentrationthe reaction mixture was partially concentrated in vacuo
  3. custompartitioned between DCM and brine
  4. extractionThe aqueous layer was extracted with DCM (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-433a2965ad194587af768c6cc0720dfb
出典データセット
uspto-grants-2015_11
特許番号
US09174978B2

反応ノート

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