Water → N-{(R)-2-oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethyl}methanesulfonamide

HRID 1162917Notes

Reaction equation

HRID 1162917 reaction equation
[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:29])([F:28])[F:27])[NH:15][C:16]3=[O:19])=[CH:11][CH:10]=2)[CH2:4]1.N1C=CC=CC=1.[CH3:36][S:37](Cl)(=[O:39])=[O:38].O>C(Cl)Cl>[O:8]=[C:6]1[N:5]([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]([F:28])([F:27])[F:29])[NH:15][C:16]3=[O:19])=[CH:11][CH:10]=2)[CH2:4][C@H:3]([CH2:2][NH:1][S:37]([CH3:36])(=[O:39])=[O:38])[O:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 57557987HCID 57557987, compound

Product 1

HCID 57557917N-{(R)-2-oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethyl}methanesulfonamideYield 37.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The 7-((S)-5-aminomethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (30 mg, 0.07 mmol) obtained in step B was dissolved in methylene chloride (0.3 ml). Thereafter, pyridine (30 μl, 0.37 mmol) and methanesulfonyl chloride (5.8 μl, 0.07 mmol) were added to the solution, and the obtained mixture was stirred at 0° C. for 30 minutes. Thereafter, water was added to the reaction solution, and the mixture was then extracted with methylene chloride. The extract was washed with water and a saturated saline solution, and was then dried over magnesium 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), so as to obtain N-{(R)-2-oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethyl}methanesulfonamide (12.6 mg, 36%) in the form of a colorless solid.

Workup

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

Sources & evidence

ORD record
ord-9fd7353f89a843fd907b6c19e6fe40db
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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