Hydrochloric Acid → HCID 21194155, compound

HRID 565037Notes

Reaction equation

HRID 565037 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[N:20]([CH3:22])[C:19]([C:23]([O:25]CC)=[O:24])=[CH:18]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl>C(O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[N:20]([CH3:22])[C:19]([C:23]([OH:25])=[O:24])=[CH:18]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21194194HCID 21194194, compound

Product 1

HCID 21194155HCID 21194155, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.12 g (0.31 mmol) of ethyl 7-[(3-tert-butoxycarbonylaminopropyl)amino]-1-methyl-2-indolecarboxylate, 2 ml of 5N potassium hydroxide aqueous solution and 5 ml of ethanol was stirred at room temperature for 2.5 hours. After 2N hydrochloric acid was gradually added to the reaction solution to render the pH 6, the reaction mixture was concentrated under reduced pressure. The residue was extracted three times with chloroform. The combined extracts were dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting residue was isolated and purified by silica gel column chromatography to give 0.079 g (72.4%) of 7-[(3-tert-butoxycarbonylaminopropyl)amino]-1-methyl-2-indolecarboxylic acid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. extractionThe residue was extracted three times with chloroform
  3. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customThe resulting residue was isolated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-ac6632bc7c1942659f10658695c7082c
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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