Hydrochloric Acid → HCID 11857097, compound

HRID 1162922Notes

Reaction equation

HRID 1162922 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][C@H:12]([O:40]C(=O)C)[C@H:13]1[O:17][C:16](=[O:18])[N:15]([C:19]2[CH:28]=[C:27]3[C:22]([CH:23]=[C:24]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:36]([F:39])([F:38])[F:37])[NH:25][C:26]3=[O:29])=[CH:21][CH:20]=2)[CH2:14]1)(=O)C.Cl>CO>[OH:40][C@H:12]([C@H:13]1[O:17][C:16](=[O:18])[N:15]([C:19]2[CH:28]=[C:27]3[C:22]([CH:23]=[C:24]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:36]([F:37])([F:39])[F:38])[NH:25][C:26]3=[O:29])=[CH:21][CH:20]=2)[CH2:14]1)[CH2:11][OH:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 57558083HCID 57558083, compound

Product 1

HCID 11857097HCID 11857097, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (17 mg, 0.121 mmol) was added to a methanol solution (2 ml) that contained the (S)-2-acetoxy-2-{(S)-2-oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-yl}ethyl acetate (25 mg, mmol) obtained in step B. The obtained mixture was stirred at a room temperature for 1.5 hours. Thereafter, the reaction solution was neutralized with 1 N hydrochloric acid, and the resultant was then extracted with methylene chloride. The extract was washed with water and a saturated saline solution, and was then dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=20:1) and preparative HPLC, so as to obtain 7-[(S)-5-((S)-1,2-dihydroxyethyl)-2-oxooxazolidin-3-yl]-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (6.7 mg, 32%).

Workup

  1. customobtained in step B
  2. extractionthe resultant was then extracted with methylene chloride
  3. washThe extract was washed with water
  4. dry with materiala saturated saline solution, and was then dried over anhydrous sodium sulfate
  5. distillationThereafter, the solvent was distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=20:1) and preparative HPLC

Sources & evidence

ORD record
ord-5eb5e6e139964bf8b9cdf9c267775846
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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