Hydrazine hydrate (1:1) → (3S,4S)-3-amino-1-(2,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone

HRID 708319Notes

Reaction equation

HRID 708319 reaction equation
[CH3:1][O:2][C:3]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[C@@H:8]([N:11]2C(=O)C3C(=CC=CC=3)C2=O)[C@H:7]1[C@@H:22]1[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]1.O.NN>CCO>[NH2:11][C@H:8]1[C@@H:7]([C@@H:22]2[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]2)[N:6]([CH2:5][C:4]2[CH:29]=[CH:30][C:31]([O:33][CH3:34])=[CH:32][C:3]=2[O:2][CH3:1])[C:9]1=[O:10]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 135748312-((2S,3S)-1-(2,4-dimethoxybenzyl)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-oxoazetidin-3-yl)isoindoline-1,3-dione

Product 1

HCID 13826540(3S,4S)-3-amino-1-(2,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of crude 2-((2S,3S)-1-(2,4-dimethoxybenzyl)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-oxoazetidin-3-yl)isoindoline-1,3-dione (631 g, 1.143 mol, assumed quantitative conversion from step 2) in EtOH (8.2 L) was added hydrazine hydrate (235 mL, 50-60%, ˜4 mol) over 20 min. The resulting mixture was heated to reflux for 3 h, cooled to rt, filtered, washed with EtOH and concentrated in vacuo. The residue was slurried in EtOAc (4 L), filtered and washed with water (2×1 L).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 3 h
  3. filtrationfiltered
  4. washwashed with EtOH
  5. concentrationconcentrated in vacuo
  6. filtrationfiltered
  7. washwashed with water (2×1 L)

Sources & evidence

ORD record
ord-8da7128bb5f74552ac857996e3fb44b9
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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