Hydrochloric Acid → HCID 69460314, compound

HRID 1351979Notes

Reaction equation

HRID 1351979 reaction equation
[OH:1][C@H:2]([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)[CH2:3][NH:4][C@H:5]([CH3:24])[CH2:6][C:7]1[C:15]2[C:10](=[C:11]([O:16][C@@H:17]([CH3:23])[C:18]([O:20]CC)=O)[CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:1][C@H:2]([C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)[CH2:3][NH:4][C@H:5]([CH3:24])[CH2:6][C:7]1[C:15]2[C:10]3=[C:11]([O:16][C@@H:17]([CH3:23])[C:18](=[O:20])[N:9]3[CH:8]=1)[CH:12]=[CH:13][CH:14]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 69458122HCID 69458122, compound

Product 1

HCID 69460314HCID 69460314, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl (2S)-2-((3-((2R)-2-(((2R)-2-hydroxy-2-pyridin-3-ylethyl)amino)propyl)-1H-indol-7-yl)oxy)propanoate.2 hydrochloride (205 mg, 0.423 mmol) in acetonitrile (8.7 ml) is added potassium carbonate (294 mg, 2.13 mmol), and the mixture is stirred at 60° C. for 4 hours. After the reaction is completed, the mixture is cooled to room temperature, and filtered. The filtrate is evaporated under reduced pressure to remove the solvent, and the obtained residue is purified by preparative thin layer chromatography (chloroform/methanol=10/1) to give the title compound (131 mg, yield: 85%).

Workup

  1. temperaturethe mixture is cooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate is evaporated under reduced pressure
  4. customto remove the solvent
  5. customthe obtained residue is purified by preparative thin layer chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-3d1ccf9f808a458e93013d7449a0506f
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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