Triethylamine → 2-Oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethyl methanesulfonate

HRID 1162901

Reaction equation

HRID 1162901 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[OH:13][CH2:14][CH:15]1[O:19][C:18](=[O:20])[N:17]([C:21]2[CH:30]=[C:29]3[C:24]([CH:25]=[C:26]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[C:38]([F:41])([F:40])[F:39])[NH:27][C:28]3=[O:31])=[CH:23][CH:22]=2)[CH2:16]1.[Cl-].[NH4+]>C(Cl)Cl.CO.CCCCCC>[CH3:8][S:9]([O:13][CH2:14][CH:15]1[O:19][C:18](=[O:20])[N:17]([C:21]2[CH:30]=[C:29]3[C:24]([CH:25]=[C:26]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[C:38]([F:40])([F:39])[F:41])[NH:27][C:28]3=[O:31])=[CH:23][CH:22]=2)[CH2:16]1)(=[O:11])=[O:10]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 575581517-(5-Hydroxymethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

Product 1

HCID 575578752-Oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethyl methanesulfonateYield 76%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

Triethylamine (128 μl) and methanesulfonyl chloride (71 μl) were added to a solution obtained by dissolving the 7-(5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (186.7 mg, 0.462 mmol) obtained in step B in methylene chloride (2.3 ml), under cooling on ice. The obtained mixture was stirred for 30 minutes. Thereafter, a saturated ammonium chloride aqueous solution was added to the reaction solution, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and was then concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1, and then methylene chloride:methanol=30:1), so as to obtain 2-oxo-3-[1-oxo-3-(2-trifluoromethylphenyl)-1,2-dihydroisoquinolin-7-yl]oxazolidin-5-ylmethyl methanesulfonate (169.1 mg; yield: 76%) in the form of a colorless foaming substance.

Workup

  1. customobtained
  2. temperatureunder cooling on ice
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationwas then concentrated
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-559eb20379a84280b24188a05a533278
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Linked notes

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