Hydrochloric Acid → HCID 69458988, compound

HRID 1351959Notes

Reaction equation

HRID 1351959 reaction equation
[OH:1][C@H:2]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[C@@H:3]([NH:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[C:12]([C:17]([O:19]CC)=[O:18])[CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[CH3:4].[OH-].[Li+].Cl>O1CCCC1.O>[OH:1][C@H:2]([C:22]1[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=1)[C@@H:3]([NH:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[C:12]([C:17]([OH:19])=[O:18])[CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69457286HCID 69457286, compound

Product 1

HCID 69458988HCID 69458988, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxy-phenyl)-1-(methyl) ethylamino]ethyl}-1H-indole-7-carboxylate (115 mg, 0.301 mmol) in tetrahydrofuran (10 mL) and water (5 mL) is added lithium hydroxide (36 mg, 1.51 mmol), and the mixture is stirred at room temperature for 15 hours. The pH value of the reaction solution is adjusted to pH 7 with 1N aqueous hydrochloric acid solution, and the solvent is distilled off. The residue is isolated by reversed phase column (octadecylsilyl, water→water-methanol=10:1→9:1→6:1) to give 3-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-(methyl)ethyl-amino]ethyl}-1H-indole-7-carboxylic acid (69.3 mg, 0.195 mmol, 65%).

Workup

  1. distillationthe solvent is distilled off
  2. customThe residue is isolated by reversed phase column (octadecylsilyl, water→water-methanol=10:1→9:1→6:1)

Sources & evidence

ORD record
ord-86fba5b08d5345318544905e95257cdc
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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