Hydrochloric Acid → HCID 69457383, compound

HRID 1351946Notes

Reaction equation

HRID 1351946 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]([O:17][CH2:18][C:19]([O-:21])=[O:20])[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]([O:17][CH2:18][C:19]([OH:21])=[O:20])[CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86604023HCID 86604023, compound

Product 1

HCID 69457383HCID 69457383, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (((3-(2-(((1S,2R)-2-hydroxy-2-(4-hydroxy-phenyl)-1-methylethyl)amino)ethyl)-1H-indol-7-yl)oxy)acetate (115 mg, 0.279 mmol) in tetrahydrofuran (5 mL) and water (0.5 mL) is added lithium hydroxide (10 mg, 0.418 mmol), and the mixture is stirred at room temperature for 11 hours. The pH value of the mixture is adjusted to pH 7 with 1N aqueous hydrochloric acid solution, and the solvent is distilled off. The obtained crude product is purified by octadecylsilyl (ODS) column chromatography (water→10% aqueous methanol) to give (((3-(2-(((1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl)amino)ethyl)-1H-indol-7-yl)oxy)acetic acid (108 mg, 0.279 mmol, yield: 100%).

Workup

  1. distillationthe solvent is distilled off
  2. customThe obtained crude product
  3. customis purified by octadecylsilyl (ODS) column chromatography (water→10% aqueous methanol)

Sources & evidence

ORD record
ord-f421e5e94f6d4a838cc1177b5e4bbe71
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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