HCID 70418165, compound → HCID 70417273, compound

HRID 414863Notes

Reaction equation

HRID 414863 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 70418165HCID 70418165, compound

Product 1

HCID 70417273HCID 70417273, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In 50 ml of methanol is dissolved 1.83 g (5 mmole) of trans-1-benzyloxy-3-(tert-butoxycarbonylamino)-4-carbamoyloxymethyl-2-azetidinone, and 190 mg of 10% palladium-charcoal is added to the solution, followed by stirring under a hydrogen atmosphere at room temperature for 30 minutes. The catalyst is filtered off, and the filtrate is concentrated under reduced pressure to give 1.32 g (96.1%) of trans-3-(tert-butoxycarbonylamino)-4-carbamoyloxymethyl-1-hydroxy-2-azetidinone as a colorless foamy product.

Workup

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

Sources & evidence

ORD record
ord-def719eeed3c4450924bb060e68f9aa6
Source dataset
uspto-grants-1988_12
Patent number
US04794108

Reaction notes

Loading…