HCID 57174922, compound → (3S,4R)-3-Amino-4-phenoxyazetidin-2-one

HRID 619709Notes

Reaction equation

HRID 619709 reaction equation
C(OC([NH:11][C@H:12]1[C@@H:15]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:14][C:13]1=[O:23])=O)C1C=CC=CC=1.[H][H]>[Pd].C1COCC1.C(OCC)(=O)C>[NH2:11][C@H:12]1[C@@H:15]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:14][C:13]1=[O:23]

Participants

6

Reactant 2

HCID 57174922HCID 57174922, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 56992325(3S,4R)-3-Amino-4-phenoxyazetidin-2-oneYield 77%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3S, 4R)-3-benzyloxycarbonylamino-4-phenoxy-azetidin-2-one (1.85 g. 5.9 mmole) is hydrogenated with 2 g of 10% palladium on activated carbon in THF (30 ml) and ethyl acetate (30 ml) at 50 psi hydrogen pressure at room temperature for 2 hours. After removal of catalyst by filtration, 810 mg of deprotected (3S, 4R)-3-amino-4-phenoxy-azetidin-2-one is obtained.

Workup

  1. customAfter removal of catalyst
  2. filtrationby filtration

Sources & evidence

ORD record
ord-a18e4a3b641b4570b9b5c825939a0f40
Source dataset
uspto-grants-1999_09
Patent number
US05959123

Reaction notes

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