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

HRID 708338Notes

Reaction equation

HRID 708338 reaction equation
[OH:1][CH2:2][C:3]1[CH:7]=[N:6][N:5]([CH2:8][C@@H:9]2[C@H:12]([NH:13]C(=O)OCC3C=CC=CC=3)[C:11](=[O:24])[NH:10]2)[N:4]=1>CCO.[Pd]>[NH2:13][C@H:12]1[C@@H:9]([CH2:8][N:5]2[N:4]=[C:3]([CH2:2][OH:1])[CH:7]=[N:6]2)[NH:10][C:11]1=[O:24]

Participants

4

Reactant 1

HCID 118411384Benzyl((2R,3S)-2-((4-(hydroxymethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate

Product 1

HCID 118380161(3S,4R)-3-amino-4-((4-(hydroxymethyl)-2H-1,2,3-triazol-2-yl)methyl)azetidin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of benzyl ((2R,3S)-2-((4-(hydroxymethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate (1.54 g, 4.65 mmol) in EtOH (50 mL) and EtOH (25 mL) was added Pd/C (10%, 0.51 g, 4.65 mmol). After stirring at rt for 4 h, the reaction mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo to afford the title compound (assume quantitive). The crude was used as such in the following step. LCMS: Rt=0.12 min, m/z=198.0 (M+1) Method 2m_acidic.

Workup

  1. filtrationthe reaction mixture was filtered through a celite pad
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-10fe5bbc5fb247f3b52ad35ed8fc3b9c
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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