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

HRID 1162901

反応式

HRID 1162901 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-559eb20379a84280b24188a05a533278
出典データセット
uspto-grants-2010_10
特許番号
US07820693B2

関連ノート

読み込み中…