HCID 15223708, compound → HCID 15223710, compound

HRID 21708Notes

Reaction equation

HRID 21708 reaction equation
C(OC([O:11][C@@H:12]([C@@H:14]1[C@@H:17]([C@H:18]([C:20]([O:22]CC2C=CC=CC=2)=[O:21])[CH3:19])[N:16]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:15]1=[O:38])[CH3:13])=O)C1C=CC=CC=1>C(O)C.[C].[Pd]>[OH:11][C@@H:12]([C@@H:14]1[C@@H:17]([C@H:18]([C:20]([OH:22])=[O:21])[CH3:19])[N:16]([CH2:30][C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[C:15]1=[O:38])[CH3:13]

Participants

4

Reactant 1

HCID 15223708HCID 15223708, compound

Product 1

HCID 15223710HCID 15223710, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A solution of (3S,4S)-3-[(1R)-1-benzyloxycarbonyloxyethyl]-4-[(1R)-1-benzyloxycarbonylethyl]-1-(t-butyloxycarbonylmethyl)azetidin-2-one (81.50 g) in ethanol (800 ml) was subjected to hydrogenation at room temperature in the presence of 10% palladium-carbon (8.15 g) under atmospheric pressure, followed by filtration to remove the catalyst. The filtrate and the washings were combined and evaporated to give (3S,4S)-3-[(1R)-1-hydroxyethyl]-4-[(1R)-1-carboxyethyl]-1-(t-butyloxycarbonylmethyl)azetidin-2-one.

Workup

  1. filtrationfollowed by filtration
  2. customto remove the catalyst
  3. customevaporated

Sources & evidence

ORD record
ord-77e51007772249408b213f576e53c828
Source dataset
uspto-grants-1995_06
Patent number
US05424422

Reaction notes

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