Potassium Hydroxide → HCID 69458810, compound

HRID 1351942Notes

Reaction equation

HRID 1351942 reaction equation
[CH2:1]([N:3]([CH2:32][CH3:33])[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[N:13]([CH3:15])[CH:12]=[C:11]2[CH2:16][C@H:17]([N:19]1[CH2:23][C@@H:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)[O:21]C1=O)[CH3:18])=[O:5])[CH3:2].[OH-].[K+]>O.C(O)C.C(Cl)(Cl)Cl>[NH3:3].[CH2:32]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[N:13]([CH3:15])[CH:12]=[C:11]2[CH2:16][C@H:17]([NH:19][CH2:23][C@@H:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=1)[OH:21])[CH3:18])=[O:5])[CH3:33]

Participants

7

Reactant 2

HCID 14797Potassium HydroxideHCID 69457291HCID 69457291, compound

Product 2

HCID 222AmmoniaHCID 69458810HCID 69458810, compoundYield 141.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of 3-{(2 R)-2-[(5R)-5-(3-chlorophenyl)-2-oxooxazolidin-3-yl]propyl}-1H-indole-7-carboxylic acid diethylamide (10 mg, 0.022 mmol), methyl iodide (21 μL, 0.33 mmol), potassium carbonate (90 mg, 0.66 mmol) in acetone (2 mL) is refluxed for 24 hours. After cooling, the insoluble materials are removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is purified by preparative TLC (silica gel, 0.5 mm, 20×20 cm, methanol/chloroform=1/30) to give 3-{(2R)-2-[(5R)-5-(3-chlorophenyl)-2-oxooxazolidin-3-yl]-propyl}-1-methyl-1H-indole-7-carboxylic acid diethylamide (3 mg). A solution of 3-{(2R)-2-[(5R)-5-(3-chlorophenyl)-2-oxooxazolidin-3-yl]-propyl}-1-methyl-1H-indole-7-carboxylic acid diethylamide (3 mg, 0.0064 mmol) and potassium hydroxide (0.6 g) in water (1 mL) and ethanol (1 mL) is stirred at 70° C. for 7 hours. After cooling, ethanol is removed by distillation, and water is added thereto. The mixture is extracted with ethyl acetate, and the organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution, dried over sodium sulfate, and concentrated. The residue is purified by silica gel column chromatography (60, 2 g, a saturated ammonia solution in chloroform) to give 3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethyl-amino]propyl}-1-methyl-1H-indole-7-carboxylic acid diethylamide (2 mg, yield: 71%).

Workup

  1. temperatureAfter cooling
  2. customethanol is removed by distillation, and water
  3. additionis added
  4. extractionThe mixture is extracted with ethyl acetate
  5. washthe organic layer is washed with a saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue is purified by silica gel column chromatography (60, 2 g

Sources & evidence

ORD record
ord-2fe410937f1d42858db5db11af831fd8
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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