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

HRID 1162917노트

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HRID 1162917 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9fd7353f89a843fd907b6c19e6fe40db
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820693B2

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