(3S,4S)-1-benzyloxy-3-(tert-butoxycarbonylamino)-4-carbamoyloxymethyl-2-azetidinone → (3S,4S)-3-(tert-butoxycarbonyl-amino)-4-carbamoyloxymethyl-1-hydroxy-2-azetidinone

HRID 414861Notes

Reaction equation

HRID 414861 reaction equation
C([O:8][N:9]1[C@H:12]([CH2:13][O:14][C:15](=[O:17])[NH2:16])[C@H:11]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:10]1=[O:26])C1C=CC=CC=1>CO.[Pd]>[C:22]([O:21][C:19]([NH:18][C@H:11]1[C@@H:12]([CH2:13][O:14][C:15](=[O:17])[NH2:16])[N:9]([OH:8])[C:10]1=[O:26])=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 1

HCID 13489000(3S,4S)-1-benzyloxy-3-(tert-butoxycarbonylamino)-4-carbamoyloxymethyl-2-azetidinone

Product 1

HCID 13489002(3S,4S)-3-(tert-butoxycarbonyl-amino)-4-carbamoyloxymethyl-1-hydroxy-2-azetidinoneYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In 10 ml of methanol is suspended 900 mg (2.46 mmole) of (3S,4S)-1-benzyloxy-3-(tert-butoxycarbonylamino)-4-carbamoyloxymethyl-2-azetidinone, and 100 mg of 10% palladium-charcoal is added to the solution, followed by stirring under a hydrogen atmosphere at room temperature for 1 hour. The catalyst is filtered off, and the filtrate is concentrated to dryness under reduced presuure to give 680 mg of (3S,4S)-3-(tert-butoxycarbonyl- amino)-4-carbamoyloxymethyl-1-hydroxy-2-azetidinone as colorless powder.

Workup

  1. additionis added to the solution
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrate is concentrated to dryness under reduced presuure

Sources & evidence

ORD record
ord-4808304107a84186b47a8bb251e5393f
Source dataset
uspto-grants-1988_12
Patent number
US04794108

Reaction notes

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