Ethylenediamine → HCID 22485685, compound

HRID 2181191Notes

Reaction equation

HRID 2181191 reaction equation
[CH2:1]([O:4][CH:5]([CH2:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15](COCC[Si](C)(C)C)[CH:14]=[CH:13]2)[C:6]([OH:8])=[O:7])[CH2:2][CH3:3].C(N)CN.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O>[NH:15]1[C:16]2[C:12](=[CH:11][C:10]([CH2:9][CH:5]([O:4][CH2:1][CH2:2][CH3:3])[C:6]([OH:8])=[O:7])=[CH:18][CH:17]=2)[CH:13]=[CH:14]1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 2724141Tetrabutylammonium FluorideHCID 22485675HCID 22485675, compound

Product 1

HCID 22485685HCID 22485685, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

0.96 g rac-2-propoxy-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-5-yl]-propionic acid were dissolved in 40 ml N,N-dimethylformamide. 0.94 ml Ethylene diamine were added, followed by 7.63 ml of a tetra-butylammonium fluoride solution (1 molar in tetrahydrofuran); a small amount of molecular sieves was then added to the reaction mixture and it was heated to 80° C. After 6 hours, the mixture was cooled to r.t., filtered and the filtrate was poured into ice water and extracted 3 times with dichloromethane. The organic phases were washed with water, dried over MgSO4, filtered again and evaporated. The crude rac-3-(1H-indol-5-yl)-2-propoxy-propionic acid was used for the next step without purification.

Workup

  1. additiona small amount of molecular sieves was then added to the reaction mixture and it
  2. temperaturethe mixture was cooled to r.t.
  3. filtrationfiltered
  4. additionthe filtrate was poured into ice water
  5. extractionextracted 3 times with dichloromethane
  6. washThe organic phases were washed with water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered again
  9. customevaporated
  10. customThe crude rac-3-(1H-indol-5-yl)-2-propoxy-propionic acid was used for the next step without purification

Sources & evidence

ORD record
ord-20fef44b9b2e4258a7eab97bd2444a5c
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

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