Acetic Acid → {3-[(2R)-2-((2R)-2-Hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}acetic acid

HRID 1351921Notes

Reaction equation

HRID 1351921 reaction equation
C(N(CC)[C:4](=[O:29])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[C:12]2[CH2:16][C@H:17]([NH:19][CH2:20][C@H:21]([OH:28])[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[CH3:18])C.[OH-].[K+].C([OH:36])C.C(O)(=O)C>O>[OH:28][C@H:21]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[CH2:20][NH:19][C@H:17]([CH3:18])[CH2:16][C:12]1[C:11]2[C:15](=[C:7]([O:6][CH2:5][C:4]([OH:29])=[O:36])[CH:8]=[CH:9][CH:10]=2)[NH:14][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 69459174N,N-diethyl-2-{3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}-acetamide

Product 1

HCID 9848117{3-[(2R)-2-((2R)-2-Hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N,N-diethyl-2-{3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indol-7-yloxy}acetamide (30 mg, 0.071 mmol) and potassium hydroxide (120 mg, 2.1 mmol) in water (1 mL)/ethanol (1 mL) is stirred at 60° C. for 6 hours. After cooling, to the mixture is added acetic acid (0.112 mL), and the mixture is concentrated. The residue is purified by preparative reversed phase HPLC (octadecylsilyl, trade name: Combiprep, ODS-A (YMC), inner diameter: 50×20 mm, particle size: 5 μm, pore size: 120 angstrom (hereinafter, this column is used in preparative reversed phase HPLC column), 0.05% trifluoroacetic acid/water-0.035% trifluoroacetic acid/acetonitrile) to give the desired {3-[(2R)-2-((2R)-2-hydroxy 2-pyridin-3-yl-ethylamino)propyl]-1H-indol-7-yloxy}acetic acid.2 trifluoroacetate (24 mg, yield: 57%).

Workup

  1. temperatureAfter cooling, to the mixture
  2. concentrationthe mixture is concentrated
  3. customThe residue is purified by preparative reversed phase HPLC (octadecylsilyl, trade name

Sources & evidence

ORD record
ord-9a4bcc636576421db98490f2b2ce531b
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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