Hydrochloric Acid → HCID 69712720, compound

HRID 1351981Notes

Reaction equation

HRID 1351981 reaction equation
C(OC([N:8]([CH2:31][C@@H:32]([C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1)[O:33][Si](CC)(CC)CC)[C@H:9]([CH3:30])[CH2:10][C:11]1[C:19]2[C:14](=[C:15]([O:20][CH:21]([CH2:27][CH2:28][CH3:29])[C:22]([O:24]CC)=[O:23])[CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=O)(C)(C)C.Cl.O>C(O)C.O1CCOCC1>[OH:33][C@H:32]([C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1)[CH2:31][NH:8][C@H:9]([CH3:30])[CH2:10][C:11]1[C:19]2[C:14](=[C:15]([O:20][CH:21]([CH2:27][CH2:28][CH3:29])[C:22]([OH:24])=[O:23])[CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 69455699HCID 69455699, compound

Product 1

HCID 69712720HCID 69712720, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the obtained ethyl 2-((3-((2R)-2-((tert-butoxy-carbonyl) ((2R)-2-pyridin-3-yl-2-((triethylsilyl)oxy)ethyl)amino)propyl)-1H-indol-7-yl)oxy)pentanoate in ethanol (0.2 ml) is added a solution of 4N-hydrogen chloride in dioxane (0.2 ml), and the mixture is stirred at room temperature for 19 hours. After the reaction is completed, water (0.2 ml) is added to the mixture, and the solvent is evaporated under reduced pressure. To a solution of the obtained residue in ethanol (0.35 ml) is added a 5N aqueous potassium hydroxide solution (0.09 ml), and the mixture is stirred at room temperature for 4 hours. After the reaction is completed, the mixture is neutralized with 1N hydrochloric acid, and the solvent is evaporated under reduced pressure. The residue is purified by preparative high performance liquid chromatography (0.035% trifluoroacetic acid/acetonitrile-0.05% trifluoroacetic acid/water) to give 2-((3-((2R)-2-(((2R)-2-hydroxy-2-pyridin-3-ylethyl)-amino)propyl)-1H-indol-7-yl)oxy)pentanoic acid.2 trifluoroacetate (13.2 mg).

Workup

  1. customthe solvent is evaporated under reduced pressure
  2. additionTo a solution of the obtained residue in ethanol (0.35 ml) is added a 5N aqueous potassium hydroxide solution (0.09 ml)
  3. stirringthe mixture is stirred at room temperature for 4 hours
  4. customthe solvent is evaporated under reduced pressure
  5. customThe residue is purified by preparative high performance liquid chromatography (0.035% trifluoroacetic acid/acetonitrile-0.05% trifluoroacetic acid/water)

Sources & evidence

ORD record
ord-8889bd2299854410a7fe8f4f99aa27ac
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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