Formic Acid → (3S,4R)-4-((1H-1,2,4-triazol-1-yl)methyl)-3-aminoazetidin-2-one

HRID 708363Notes

Reaction equation

HRID 708363 reaction equation
[N:1]1([CH2:6][C@@H:7]2[C@H:10]([NH:11]C(=O)OCC3C=CC=CC=3)[C:9](=[O:22])[NH:8]2)[CH:5]=[N:4][CH:3]=[N:2]1.C(O)=O>CO.[Pd]>[N:1]1([CH2:6][C@H:7]2[NH:8][C:9](=[O:22])[C@H:10]2[NH2:11])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 131733730Benzyl ((2R,3S)-2-((1H-1,2,4-triazol-1-yl)methyl)-4-oxoazetidin-3-yl)carbamate

Product 1

HCID 118390218(3S,4R)-4-((1H-1,2,4-triazol-1-yl)methyl)-3-aminoazetidin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl ((2R,3S)-2-((1H-1,2,4-triazol-1-yl)methyl)-4-oxoazetidin-3-yl)carbamate (38 mg, 0.126 mmol) in MeOH (5 mL) was added Pd black (6.7 mg, 0.063 mmol) followed by formic acid (339 μL, 8.83 mmol). After 1 h of stirring, the mixture was filtered over celite, washing with MeOH, and the filtrate was concentrated in vacuo. The solution was lyophilized and the crude material was used directly in the subsequent step. LCMS: Rt=0.14 min, m/z=168.1 (M+1) Method 2m_acidic.

Workup

  1. filtrationthe mixture was filtered over celite
  2. washwashing with MeOH
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c8969494f32d4c5396fb4f534ffa6259
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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