(3s-trans)-3-[(t-Butyloxycarbonyl)amino]-4-methyl-2-oxo-1-(phenylmethoxy)azetidine → tert-butyl N-[(2S,3S)-1-hydroxy-2-methyl-4-oxoazetidin-3-yl]carbamate

HRID 2165282Notes

Reaction equation

HRID 2165282 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:12]([CH3:13])[N:11]([O:14]CC2C=CC=CC=2)[C:10]1=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:12]([CH3:13])[N:11]([OH:14])[C:10]1=[O:22])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 12946599(3s-trans)-3-[(t-Butyloxycarbonyl)amino]-4-methyl-2-oxo-1-(phenylmethoxy)azetidine

Product 1

HCID 12946603tert-butyl N-[(2S,3S)-1-hydroxy-2-methyl-4-oxoazetidin-3-yl]carbamateYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10.5 g of (3S-trans)-3-(t-Butyloxycarbonylamino)-1-benzyloxy-4-methyl-2-azetidinone was dissolved in 250 ml of methanol and hydrogenated with 1.43 g of palladium on carbon (10%) as the catalyst. After 45 minutes the catalyst was filtered off and the filtrate was evaporated in vacuo. The crystalline title compound was dried (vacuum desiccator) at room temperature yielding 7.3 g of the title compound, melting point 161°-162° C., dec.

Workup

  1. filtrationAfter 45 minutes the catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. dry with materialThe crystalline title compound was dried (vacuum desiccator) at room temperature

Sources & evidence

ORD record
ord-ab5a250fe8a941e19df62f2d24e5e752
Source dataset
uspto-grants-1990_07
Patent number
US04939253

Reaction notes

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