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Hydrochloric Acid → 7-(5-aminomethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1162903
ノート
印刷プレビュー

反応式

HRID 1162903 の反応式
[N:1]([CH2:4][CH:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[C:16]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([F:31])([F:30])[F:29])[NH:17][C:18]3=[O:21])=[CH:13][CH:12]=2)[CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.Cl>O1CCCC1>[NH2:1][CH2:4][CH:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[C:16]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([F:29])([F:31])[F:30])[NH:17][C:18]3=[O:21])=[CH:13][CH:12]=2)[CH2:6]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11776TriphenylphosphineHCID 118541917-(5-azidomethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

生成物 1

HCID 118541927-(5-aminomethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one収率 98%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
40 °C

実験手順

The 7-(5-azidomethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (50.0 mg, 0.116 mmol) obtained in Example 1-30 was dissolved in tetrahydrofuran (387 μl). Thereafter, triphenylphosphine (33.6 mg, 0.128 mmol) and water (20.9 μl) were added to the obtained solution, and the obtained mixture was then stirred at 40° C. for 14 hours. Thereafter, 1 N hydrochloric acid (0.5 ml) was added to the reaction solution, followed by washing with ethyl acetate. A 1 N sodium hydroxide aqueous solution (1.0 ml) was added to the residual water layer, followed by extraction with ethyl acetate. The extract was washed with a saturated saline solution, and was then dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The obtained residue was purified by column chromatography using Bond Elut (registered trademark) NH2 (Varian; 1g), so as to obtain 7-(5-aminomethyl-2-oxooxazolidin-3-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (45.8 mg; yield: 98%) in the form of a colorless foaming substance.

後処理

  1. washby washing with ethyl acetate
  2. additionA 1 N sodium hydroxide aqueous solution (1.0 ml) was added to the residual water layer
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with a saturated saline solution
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe obtained residue was purified by column chromatography

出典と根拠

ORDレコード
ord-2f49e85d4f5d483796b1b5dc23eca415
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07820693B2

反応ノート

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