Trifluoroacetic acid → HCID 18926565, compound

HRID 1600195Notes

Reaction equation

HRID 1600195 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][CH2:16][CH2:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:22]=[C:21]2[CH2:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1)=O)(C)(C)C>ClCCl>[NH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:22]=[C:21]2[CH2:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 54155207HCID 54155207, compound

Product 1

HCID 18926565HCID 18926565, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 ml) was added to a stirred solution of methyl 5-(2-t-butoxycarbonylaminoethyl)-3-(3-pyridylmethyl)-1H-indole -1-propanoate (5.0 g) in dry dichloromethane (50 ml) and the solution was stirred for 3 hours. An additional 5 ml of trifluoroacetic acid was then added and stirring was continued for a further 2 hours. The solution was evaporated and the residue was partitioned between dichloromethane and dilute aqueous ammonia. The aqueous layer was separated and extracted withdichloromethane. The organic layers were combined and evaporated. Water (ca50 ml) was added followed by sufficient acetic acid to adjust the pH to ca4. The solution was washed twice with ethyl acetate and then made basic with concentrated aqueous ammonia solution. The mixture was extracted twice with dichloromethane and the combined extracts were dried (MgSO4) and evaporated to give the title compound as a gum (2.51 g), Rf. 0.15(SS3).

Workup

  1. stirringstirring
  2. waitwas continued for a further 2 hours
  3. customThe solution was evaporated
  4. customthe residue was partitioned between dichloromethane and dilute aqueous ammonia
  5. customThe aqueous layer was separated
  6. extractionextracted withdichloromethane
  7. customevaporated
  8. additionWater (ca50 ml) was added
  9. washThe solution was washed twice with ethyl acetate
  10. extractionThe mixture was extracted twice with dichloromethane
  11. dry with materialthe combined extracts were dried (MgSO4)
  12. customevaporated

Sources & evidence

ORD record
ord-133345db662b4d62a38f9cb95da5c7f3
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

Loading…