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

HRID 708452노트

반응식

HRID 708452 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-433a2965ad194587af768c6cc0720dfb
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174978B2

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