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 1383352노트

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HRID 1383352 반응식
[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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

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온도
0 °C

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-8896528be98c490dbd9c121899bb42ba
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06255304B1

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