Benzyl ((2R,3S)-2-((1H-1,2,4-triazol-1-yl)methyl)-4-oxoazetidin-3-yl)carbamate → (3S,4R)-4-((1H-1,2,4-triazol-1-yl)methyl)-3-aminoazetidin-2-one

HRID 708377Notes

Reaction equation

HRID 708377 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>CCO.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

4

Reactant 1

HCID 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 18681192Ethanol, mixt. with methanolSolvent

Procedure

Prepared in an analogous manner to example 4, step 3 using benzyl ((2R,3S)-2-((1H-1,2,4-triazol-1-yl)methyl)-4-oxoazetidin-3-yl)carbamate (250 mg, 0.830 mmol) and Pd on C (10%, 125 mg) in EtOH:MeOH (4:1, 8.3 mL) for 3 h. The crude residue was used as such in following step. LCMS: Rt=0.13 min, m/z=168.1 (M+1) Method 2m_acidic.

Sources & evidence

ORD record
ord-e0ccdae725bf46bea5460486373827b6
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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