Methanol → HCID 21098827, compound

HRID 1351952Notes

Reaction equation

HRID 1351952 reaction equation
[OH:1][C@H:2]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:3][NH:4][C@H:5]([CH3:20])[CH2:6][C:7]1[C:15]2[C:10](=[C:11]([C:16]([O:18]C)=[O:17])[CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1.[OH-].[K+].CO>O>[OH:1][C@H:2]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:3][NH:4][C@H:5]([CH3:20])[CH2:6][C:7]1[C:15]2[C:10](=[C:11]([C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 69458821HCID 69458821, compound

Product 1

HCID 21098827HCID 21098827, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-yl-ethylamino)propyl]-1H-indole-7-carboxylate (440 mg, 1.24 mmol) and potassium hydroxide (1.14 g, 20 mmol) in water (2 mL)/methanol (10 mL) is stirred at room temperature for 19 hours. After concentrated, the resultant is purified by reversed phase column chromatography (octadecylsilyl, trifluoroacetic acid/water/methanol) to give the desired 3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)propyl]-1H-indole-7-carboxylic acid.2 trifluoroacetate (560 mg, yield: 80%).

Workup

  1. concentrationAfter concentrated
  2. customthe resultant is purified by reversed phase column chromatography (octadecylsilyl, trifluoroacetic acid/water/methanol)

Sources & evidence

ORD record
ord-3fe8ad17315d48c1ab9e51fcd55786e5
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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