Acetic Anhydride → HCID 57558083, compound

HRID 1162921Notes

Reaction equation

HRID 1162921 reaction equation
CS([O:5][CH2:6][C@@H:7]([O:35]S(C)(=O)=O)[C@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]([F:34])([F:33])[F:32])[NH:20][C:21]3=[O:24])=[CH:16][CH:15]=2)[CH2:9]1)(=O)=O.[C:40]([O-:43])(=O)[CH3:41].[K+].C(=O)(O)[O-].[Na+].[C:50](OC(=O)C)(=[O:52])[CH3:51]>>[C:50]([O:5][CH2:6][C@H:7]([O:35][C:40](=[O:43])[CH3:41])[C@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]([F:34])([F:33])[F:32])[NH:20][C:21]3=[O:24])=[CH:16][CH:15]=2)[CH2:9]1)(=[O:52])[CH3:51]

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 517044Potassium AcetateHCID 57558161HCID 57558161, compound

Product 1

HCID 57558083HCID 57558083, compoundYield 54%

Conditions

Temperature
120 °C

Procedure

The (R)-2-methanesulfonyloxy-2-{(S)-2-oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-yl}ethyl methanesulfonate (53 mg, 0.0897 mmol) obtained in step A was dissolved in acetic anhydride (1 ml). Thereafter, potassium acetate (44 mg, 0.449 mmol) was added to the solution, and the obtained mixture was then stirred at 120° C. for 6 hours. The reaction solution was cooled to a room temperature. A saturated sodium bicarbonate aqueous solution was added thereto, and the obtained mixture was then extracted with ethyl acetate. 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=50:1), so as to obtain (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, 54%).

Workup

  1. temperatureThe reaction solution was cooled to a room temperature
  2. extractionthe obtained mixture was then extracted with ethyl acetate
  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=50:1)

Sources & evidence

ORD record
ord-80c0863b450a420582616918f78a8a5b
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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