(1S)-(+)-Camphor-10-sulphonic acid → (1r,6s)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane-(1S)-camphorsulfonic acid salt

HRID 413466Notes

Reaction equation

HRID 413466 reaction equation
[CH2:1]([N:8]1[C:16](=[O:17])[C@@H:15]2[C@@H:10]([CH2:11][CH2:12][CH2:13][NH:14]2)[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C@:19]12([CH2:29][S:30]([OH:33])(=[O:32])=[O:31])[C:26]([CH3:28])([CH3:27])[CH:23]([CH2:24][CH2:25]1)[CH2:22][C:20]2=[O:21]>CC(C)=O>[C@:19]12([CH2:29][S:30]([OH:33])(=[O:31])=[O:32])[C:26]([CH3:28])([CH3:27])[CH:23]([CH2:24][CH2:25]1)[CH2:22][C:20]2=[O:21].[CH2:1]([N:8]1[C:16](=[O:17])[C@H:15]2[C@H:10]([CH2:11][CH2:12][CH2:13][NH:14]2)[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 7472044cis-8-Benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane

Product 1

HCID 86758982(1r,6s)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane-(1S)-camphorsulfonic acid saltYield 42%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.53 g (2.18 mmol) of cis-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane (racemate) and 0.51 g (2.18 mmol) of (1S)-camphorsulfonic acid are dissolved in 30 ml of acetone under reflux to give a clear solution and cooled to room temperature. The precipitated solid is filtered off with suction and dried in vacuo to give 0.23 g (0.49 mmol) of (1R,6S)-8-benzyl-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane-(1S)-camphorsulfonic acid salt.

Workup

  1. temperatureunder reflux
  2. customto give a clear solution
  3. filtrationThe precipitated solid is filtered off with suction
  4. customdried in vacuo

Sources & evidence

ORD record
ord-eb867e8450464a01a25968dba17c8262
Source dataset
uspto-grants-2003_05
Patent number
US06566523B1

Reaction notes

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