Trifluoroacetic acid → HCID 178512984, compound

HRID 2302015Notes

Reaction equation

HRID 2302015 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([NH2:23])=[NH:22])[CH:13]=2)[NH:8][C:7]1=[O:24])C.[OH-].[Na+].FC(F)(F)C(O)=O>C(O)C>[NH:20]([CH2:19][CH2:18][CH2:17][O:16][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:24])[CH:6]([CH2:5][C:4]([OH:25])=[O:3])[CH2:15]2)[C:21]([NH2:23])=[NH:22]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 178470584HCID 178470584, compound

Product 1

HCID 178512984HCID 178512984, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [6-(3-Guanidino-propoxy)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic acid ethyl ester (0.76 g, 1.6 mmol) in ethanol (7 mL) was treated with 0.5 N aqueous NaOH and heated at reflux for 3 h. The resulting precipitate was cooled to room temperature, treated with trifluoroacetic acid (1.5 mL) and the solution thus formed concentrated in vacuo to yield a clear, colorless oil. Purification by reverse phase HPLC gave the title compound (0.38 g, 55% yield) as a fluffy white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customthe solution thus formed
  4. concentrationconcentrated in vacuo
  5. customto yield a clear, colorless oil
  6. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-91d348707bf4402088d5b8640d2e391a
Source dataset
uspto-grants-2002_08
Patent number
US06429214B1

Reaction notes

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