1,1'-Thiocarbonyldi-2(1H)-pyridone → (S)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-isothiocyanatomethyl-2-oxazolidinone

HRID 1383352ノート

反応式

HRID 1383352 の反応式
[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[F:17][C:18]1[CH:19]=[C:20]([N:32]2[CH2:36][C@H:35]([CH2:37][NH2:38])[O:34][C:33]2=[O:39])[CH:21]=[CH:22][C:23]=1[CH:24]1[CH2:29][CH2:28][S:27](=[O:31])(=[O:30])[CH2:26][CH2:25]1>C(Cl)Cl>[F:17][C:18]1[CH:19]=[C:20]([N:32]2[CH2:36][C@@H:35]([CH2:37][N:38]=[C:1]=[S:2])[O:34][C:33]2=[O:39])[CH:21]=[CH:22][C:23]=1[CH:24]1[CH2:25][CH2:26][S:27](=[O:30])(=[O:31])[CH2:28][CH2:29]1

参加物

4

反応物 2

HCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 54349937(5S)-(-)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-aminomethyl-2-oxazolidinone

生成物 1

HCID 53890370(S)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-isothiocyanatomethyl-2-oxazolidinone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
0 °C

実験手順

A solution of 1,1′-thiocarbonyldi-2(1H)-pyridone (304 mg, 1.31 mmol) in anhydrous methylene chloride (13 mL) at 0° C. under a nitrogen atmosphere was treated with a solution of (S)-(−)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-aminomethyl-2-oxazolidinone, as prepared in Example 11, Step 1, (375 mg, 1.09 mmol) in anhydrous methylene chloride (88 mL) over 30 minutes. The resulting mixture was stirred at 0° C. for 30 minutes and at ambient temperature for 30 minutes and was then diluted with methylene chloride (40 mL), washed with water (25 mL) and brine (25 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was chromatographed on silica gel (230-400 mesh, 45 g), eluting with acetonitrile/methylene chloride (7.5/92.5), and those fractions with an Rf=0.64 by TLC (acetonitrile/methylene chloride, 20/80) were pooled and concentrated to give (S)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-isothiocyanatomethyl-2-oxazolidinone, mp 158-162° C. (dec.).

後処理

  1. washwashed with water (25 mL) and brine (25 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was chromatographed on silica gel (230-400 mesh, 45 g)
  5. washeluting with acetonitrile/methylene chloride (7.5/92.5)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-8896528be98c490dbd9c121899bb42ba
出典データセット
uspto-grants-2001_07
特許番号
US06255304B1

反応ノート

読み込み中…