Sodium Hydroxide → HCID 69458777, compound

HRID 1351966Notes

Reaction equation

HRID 1351966 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]2[O:12]C(=O)[N:10]([C@H:14]([CH3:30])[CH2:15][C:16]3[C:24]4[C:19](=[C:20]([NH:25][C:26](=[O:29])[CH2:27][CH3:28])[CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:12])[CH2:9][NH:10][C@H:14]([CH3:30])[CH2:15][C:16]2[C:24]3[C:19](=[C:20]([NH:25][C:26](=[O:29])[CH2:27][CH3:28])[CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69457249HCID 69457249, compound

Product 1

HCID 69458777HCID 69458777, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(3-((2R)-2-((5R)-5-(3-chlorophenyl)-2-oxo-1,3-oxazolidin-3-yl)propyl)-1H-indol-7-yl)propanamide (28.4 mg, 0.0666 mmol) in ethanol (1 mL) is added a 5N aqueous sodium hydroxide solution (0.2 mL), and the mixture is stirred at room temperature for 15 hours, and further stirred at 60° C. for 11 hours. The ethanol is evaporated, and the resulting residue is separated into a saturated aqueous sodium hydrogen carbonate solution-and chloroform. The organic layer is washed with a saturated brine, and dried over anhydrous sodium sulfate. The solvent is evaporated, and the obtained crude product is purified by preparative HPLC (water-aceto-nitrile-trifluoroacetic acid), and preparative thin layer chromatography (1st; a saturated ammonia solution in chloroform-methanol=10:1, 2nd; chloroform:methanol=10: 1) to give the title compound (3.3 mg, 12.5%).

Workup

  1. stirringfurther stirred at 60° C. for 11 hours
  2. customThe ethanol is evaporated
  3. customthe resulting residue is separated into a saturated aqueous sodium hydrogen carbonate solution-and chloroform
  4. washThe organic layer is washed with a saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent is evaporated
  7. customthe obtained crude product
  8. customis purified by preparative HPLC (water-aceto-nitrile-trifluoroacetic acid), and preparative thin layer chromatography (1st

Sources & evidence

ORD record
ord-e9a3ba04c76e490197eb95fcf7b596ce
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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