Benzyl ((3S,4R)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidin-3-yl)carbamate → 3-(((2R,3S)-3-amino-4-oxoazetidin-2-yl)methyl)oxazolidin-2-one

HRID 708316Notes

Reaction equation

HRID 708316 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[CH2:22][CH2:21][O:20][C:19]2=[O:23])[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[CH2:22][CH2:21][O:20][C:19]1=[O:23]

Participants

4

Reactant 1

HCID 118411330Benzyl ((3S,4R)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidin-3-yl)carbamate

Product 1

HCID 1183800183-(((2R,3S)-3-amino-4-oxoazetidin-2-yl)methyl)oxazolidin-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 ((3S,4R)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidin-3-yl)carbamate (96 mg, 0.30 mmol) and Pd/C 10% Degussa type 101 (10%, 64 mg) in EtOH:MeOH (4:1, 1.5 mL) for 1 h. The crude residue was used as such in following step. LCMS: Rt=0.11 min, m/z=186.0 (M+1) Method 2m_acidic.

Sources & evidence

ORD record
ord-fe6df5fc57114f3aac3c2bb2bb9b8501
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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