Hydrochloric Acid → HCID 69456223, compound

HRID 1351956Notes

Reaction equation

HRID 1351956 reaction equation
C(N(CC)[C:4]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH2:15][C@H:16]([NH:18][CH2:19][C@@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[OH:21])[CH3:17])=[CH:11][NH:12]2)=[CH:8][CH:7]=1)=[O:5])C.Cl.[O:32]1CCOCC1>>[Cl:28][C:24]1[CH:23]=[C:22]([C@@H:20]([OH:21])[CH2:19][NH:18][C@H:16]([CH3:17])[CH2:15][C:10]2[C:9]3[C:13](=[CH:14][C:6]([C:4]([OH:5])=[O:32])=[CH:7][CH:8]=3)[NH:12][CH:11]=2)[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 69455783HCID 69455783, compound

Product 1

HCID 69456223HCID 69456223, compoundYield 44%

Procedure

To a solution of 3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxy-ethylamino]propyl}-1H-indole-6-carboxylic acid diethylamide (800 mg, 1.87 mmol) in 1,4-dioxane (10 ml) is added 6N—HCl (10 ml), and the mixture is refluxed for 24 hours. After allowed to cool, the reaction solution is concentrated under reduced pressure, and the residue is purified by octadecylsilyl column chromatography (trifluoroacetic acid/methanol/water), and further crystallized from aqueous methanol (pH 7) to give 3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]-propyl}-1H-indole-6-carboxylic acid (304 mg, 0.815 mmol, 44%) as white crystals.

Workup

  1. temperaturethe mixture is refluxed for 24 hours
  2. temperatureto cool
  3. concentrationthe reaction solution is concentrated under reduced pressure
  4. customthe residue is purified by octadecylsilyl column chromatography (trifluoroacetic acid/methanol/water)
  5. customfurther crystallized from aqueous methanol (pH 7)

Sources & evidence

ORD record
ord-164b88a3aaca43d2afc236c814b8fe24
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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