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Sulfuryl chloride → (5R)-3-(4-(1-Isopropylsulfonyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluoro-phenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one

HRID 723799
ノート
印刷プレビュー

反応式

HRID 723799 の反応式
Cl.[NH:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[CH:23][N:22]=[N:21]4)[O:16][C:15]3=[O:25])=[CH:10][C:9]=2[F:26])=[CH:4][CH2:3]1.C(=O)(O)[O-].[Na+].[CH:32]([S:35](Cl)(=[O:37])=[O:36])([CH3:34])[CH3:33].S(Cl)(Cl)(=O)=O>O.CC(C)=O>[CH:32]([S:35]([N:2]1[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][N:20]4[CH:24]=[CH:23][N:22]=[N:21]4)[O:16][C:15]3=[O:25])=[CH:10][C:9]=2[F:26])=[CH:4][CH2:3]1)(=[O:37])=[O:36])([CH3:34])[CH3:33]
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

7

反応物 4

HCID 24648Sulfuryl chlorideHCID 824082-Propanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 69364214(5R)-3-(4-(1,2,5,6-Tetrahydropyridin-4-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-oxazolidin-2-one hydrochloride

生成物 1

HCID 69366716(5R)-3-(4-(1-Isopropylsulfonyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluoro-phenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one
収率 45.6%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

(5R)-3-(4-(1,2,5,6-Tetrahydropyridin-4-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-oxazolidin-2-one hydrochloride (380 mg, 1 mM) was dissolved in water (5 ml), which was then diluted with acetone (10 ml), and solid sodium bicarbonate (0.84 g, 10 mM) added. The mixture was stirred and cooled to 0° C., and isopropylsulfonyl chloride (285 mg, 2 mM) added dropwise. After stirring for 5 hours, an equal portion of sulfonyl chloride was added, and stirring continued for 18 hours. Most acetone was removed by evaporation, the residue diluted with water (50 ml), and extracted with ethyl acetate (3×20 ml). The extracts were washed with brine and dried (magnesium sulfate). The residual oil after evaporation was purified by chromatography on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 5% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (205 mg).

後処理

  1. additionadded
  2. stirringAfter stirring for 5 hours
  3. stirringstirring
  4. customMost acetone was removed by evaporation
  5. additionthe residue diluted with water (50 ml)
  6. extractionextracted with ethyl acetate (3×20 ml)
  7. washThe extracts were washed with brine
  8. dry with materialdried (magnesium sulfate)
  9. customThe residual oil after evaporation
  10. customwas purified by chromatography on a 10 g silica Mega Bond Elut® column
  11. washeluting with
  12. temperaturea gradient increasing in polarity from 0 to 5% methanol in dichloromethane
  13. customevaporated

出典と根拠

ORDレコード
ord-47e740d465ec44c3b8a2abaa00d76422
出典データセット
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07141583B2

反応ノート

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