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

HRID 708452Notes

Reaction equation

HRID 708452 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-433a2965ad194587af768c6cc0720dfb
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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