N,N'-Diisopropylethylenediamine → Benzoic Acid

HRID 2212885Notes

Reaction equation

HRID 2212885 reaction equation
C(N([CH:7]([CH3:9])[CH3:8])CC)(C)C.[CH:10](NCCNC(C)C)([CH3:12])[CH3:11].FC(F)(F)[C:22]([OH:24])=[O:23].O>CS(C)=O>[C:22]([OH:24])(=[O:23])[C:8]1[CH:7]=[CH:9][CH:12]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 77628N,N'-DiisopropylethylenediamineHCID 81531DiisopropylethylamineHCID 22392675Trifluoroacetic acid water

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

50 ml of DMSO, 2 ml of diisopropylethylamine and 5 ml of N,N′-diisopropylethylenediamine were added to the resin obtained in step 1 to conduct the reaction at 60° C. for 3 days. The reaction solution was removed. The resin was washed with DMSO, DMF and dichloromethane 3 times each and then dried under reduced pressure. 5 g of Fmoc-succinimide and 25 ml of NMP were added to the obtained resin, and they were stirred at room temperature for 16 hours. The superfluous solvent was removed. The resin was washed with DMF 3 times, with dichloromethane 3 times, with NMP twice and again with dichloromethane 3 times, and then dried under reduced pressure. The resin thus obtained was treated with 500 μl of trifluoroacetic acid/water (95/5) for 1 hour. The resin was taken by the filtration and then washed with trifluoroacetic acid. The wash solutions were combined together, concentrated and purified by the reversed-phase HPLC (ODS column, developer: water (containing 0.05% of TFA) and acetonitrile (containing 0.05% of TFA) to obtain a benzoic acid derivative having a partial structure in Example 28.

Workup

  1. customthe reaction at 60° C. for 3 days
  2. customThe reaction solution was removed
  3. washThe resin was washed with DMSO, DMF and dichloromethane 3 times each and
  4. customthen dried under reduced pressure
  5. addition5 g of Fmoc-succinimide and 25 ml of NMP were added to the obtained resin, and they
  6. customThe superfluous solvent was removed
  7. washThe resin was washed with DMF 3 times, with dichloromethane 3 times, with NMP twice
  8. dry with materialagain with dichloromethane 3 times, and then dried under reduced pressure
  9. customThe resin thus obtained
  10. filtrationThe resin was taken by the filtration
  11. washwashed with trifluoroacetic acid
  12. concentrationconcentrated
  13. custompurified by the reversed-phase HPLC (ODS column, developer

Sources & evidence

ORD record
ord-772a485728ef4c8aa801508c5b13aa1c
Source dataset
uspto-grants-2006_09
Patent number
US07105520B2

Reaction notes

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