HCID 70418273, compound → HCID 70417468, compound

HRID 414864Notes

Reaction equation

HRID 414864 reaction equation
C([O:8][N:9]1[C@@H:12]([C:13](=[O:15])[NH2:14])[C@H:11]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10]1=[O:24])C1C=CC=CC=1>CO.[Pd]>[C:20]([O:19][C:17]([NH:16][C@H:11]1[C@H:12]([C:13](=[O:15])[NH2:14])[N:9]([OH:8])[C:10]1=[O:24])=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 1

HCID 70418273HCID 70418273, compound

Product 1

HCID 70417468HCID 70417468, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In 200 ml of methanol is suspended 3.69 g (11 mmole) of trans-1-benzyloxy-3-(tert-butoxycarbonylamino)-4-carbamoyl-2-azetidinone, and 350 mg of 10% palladium-charcoal is added to the suspension, followed by stirring under a hydrogen atmosphere at room temperature for 30 minutes. The catalyst is filtered off, and the filtrate is concentrated to dryness under reduced pressure to give 2.7 g of trans-3-(tert-butoxycarbonylamino)-4-carbamoyl-1-hydroxy-2-azetidinone as a yellowish foamy product.

Workup

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

Sources & evidence

ORD record
ord-ca448b37d0ce482f901a58f30db149a5
Source dataset
uspto-grants-1988_12
Patent number
US04794108

Reaction notes

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