(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 279810Notes

Reaction equation

HRID 279810 reaction equation
C([O:8][N:9]1[C@@H:12]([CH3:13])[C@H:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]1=[O:22])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[C:18]([O:17][C:15]([NH:14][C@H:11]1[C@H:12]([CH3:13])[N:9]([OH:8])[C:10]1=[O:22])=[O:16])([CH3:20])([CH3:19])[CH3:21]

Participants

5

Reactant 2

HCID 12946599(3s-trans)-3-[(t-Butyloxycarbonyl)amino]-4-methyl-2-oxo-1-(phenylmethoxy)azetidineHCID 178418361HCID 178418361, compound

Product 1

HCID 12946603tert-butyl N-[(2S,3S)-1-hydroxy-2-methyl-4-oxoazetidin-3-yl]carbamateYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 9.18 g of (3S-trans)-N-benzyloxy-3-t-butoxycarbonylamino-4-methylazetidinone in 300 ml of 95% ethanol was stirred in an atmosphere of hydrogen with 1.85 g of 1% palladium on charcoal. After 141 minutes the slurry was filtered and evaporated in vacuo. The residue was recrystallized from ether-hexane to yield 5.12 g of the title compound.

Workup

  1. filtrationAfter 141 minutes the slurry was filtered
  2. customevaporated in vacuo
  3. customThe residue was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-e4924846e6e54c39a51ca0da74561b08
Source dataset
uspto-grants-1986_05
Patent number
US04587047

Reaction notes

Loading…