Benzyl ((2R,3S)-2-((5-methyl-1H-tetrazol-1-yl)methyl)-4-oxoazetidin-3-yl)carbamate → (3S,4R)-3-amino-4-((5-methyl-1H-tetrazol-1-yl)methyl)azetidin-2-one

HRID 708359Notes

Reaction equation

HRID 708359 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C@@H:8]2[C@H:11]([NH:12]C(=O)OCC3C=CC=CC=3)[C:10](=[O:23])[NH:9]2)[N:5]=[N:4][N:3]=1>CCO.CO.[Pd]>[NH2:12][C@H:11]1[C@@H:8]([CH2:7][N:6]2[C:2]([CH3:1])=[N:3][N:4]=[N:5]2)[NH:9][C:10]1=[O:23]

Participants

4

Reactant 1

HCID 131733728Benzyl ((2R,3S)-2-((5-methyl-1H-tetrazol-1-yl)methyl)-4-oxoazetidin-3-yl)carbamate

Product 1

HCID 118379653(3S,4R)-3-amino-4-((5-methyl-1H-tetrazol-1-yl)methyl)azetidin-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-((5-methyl-1H-tetrazol-1-yl)methyl)-4-oxoazetidin-3-yl)carbamate (97 mg, 0.31 mmol) and Pd on C (10%, 50 mg) in EtOH:MeOH (5:1, 3.0 mL) for 3 h. The crude residue was used as such in following step. LCMS: Rt=0.11 min, m/z=183.2 (M+1) Method 2m_acidic.

Sources & evidence

ORD record
ord-54a50fd8445c40fdb720e111d70ca18c
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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