Benzyl ((3S,4R)-2-oxo-4-((2-oxopyridin-1(2H)-yl)methyl)azetidin-3-yl)carbamate → 1-(((2R,3S)-3-amino-4-oxoazetidin-2-yl)methyl)piperidin-2-one

HRID 708374Notes

Reaction equation

HRID 708374 reaction equation
[O:1]=[C:2]1[C@@H:5]([NH:6]C(=O)OCC2C=CC=CC=2)[C@@H:4]([CH2:17][N:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]2=[O:24])[NH:3]1>CCO.CO.[Pd]>[NH2:6][C@@H:5]1[C:2](=[O:1])[NH:3][C@@H:4]1[CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C:19]1=[O:24]

Participants

4

Reactant 1

HCID 131733739Benzyl ((3S,4R)-2-oxo-4-((2-oxopyridin-1(2H)-yl)methyl)azetidin-3-yl)carbamate

Product 1

HCID 1183802481-(((2R,3S)-3-amino-4-oxoazetidin-2-yl)methyl)piperidin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

Prepared according to example 7, step 3. A solution of benzyl ((3S,4R)-2-oxo-4-((2-oxopyridin-1(2H)-yl)methyl)azetidin-3-yl)carbamate (157 mg, 0.480 mmol) in EtOH:MeOH (5:1, 4.8 mL) was evaculated and backfilled with argon (2×) followed by addition of Pd on C (10%, 33 mg). The system was evacuated and backfilled with H2 (3×). After 3 h of stirring the mixture was filtered over celite, washing with MeOH and concentrated in vacuo. The crude residue was used as such in following step.

Workup

  1. customPrepared
  2. customThe system was evacuated
  3. filtrationwas filtered over celite
  4. washwashing with MeOH
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b756fb70faf410dabdf39a7689e4a22
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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