Sodium Fluoride → (S)-N-[[3-[3-Fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide

HRID 324564ノート

反応式

HRID 324564 の反応式
[C:1](SCC)(=[S:3])[CH3:2].[F-].[Na+].[F:9][C:10]1[CH:11]=[C:12]([N:24]2[CH2:28][C@H:27]([CH2:29][NH2:30])[O:26][C:25]2=[O:31])[CH:13]=[CH:14][C:15]=1[CH:16]1[CH2:21][CH2:20][S:19](=[O:23])(=[O:22])[CH2:18][CH2:17]1.[OH-].[K+]>C(O)C.C(Cl)Cl>[F:9][C:10]1[CH:11]=[C:12]([N:24]2[CH2:28][C@H:27]([CH2:29][NH:30][C:1](=[S:3])[CH3:2])[O:26][C:25]2=[O:31])[CH:13]=[CH:14][C:15]=1[CH:16]1[CH2:17][CH2:18][S:19](=[O:22])(=[O:23])[CH2:20][CH2:21]1

参加物

7

反応物 4

HCID 5235Sodium Fluoride2 回HCID 14797Potassium Hydroxide2 回HCID 70093Ethyl dithioacetate2 回HCID 54349937(5S)-(-)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-aminomethyl-2-oxazolidinone

生成物 1

HCID 57276083(S)-N-[[3-[3-Fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒3 回HCID 6344Dichloromethane溶媒

実験手順

A solution of ethyl dithioacetate (100 mL, 0.876 mmol) and sodium fluoride (37 mg, 0.876 mmol) in ethanol (8.8 mL) under a nitrogen atmosphere was treated with a mixture of (S)-(−)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-aminomethyl-2-oxazolidinone, as prepared in Step 1, (300 mg, 0.876 mmol) and aqueous potassium hydroxide (1M, 0.88 mL) in ethanol (43.8 mL). The resulting mixture was stirred at ambient temperature for 26 hours, during which additional ethyl dithioacetate (50 mL, 0.438 mmol), sodium fluoride (19 mg, 0.438 mmol), aqueous potassium hydroxide (1M, 0.44 mL) and ethanol (3.0 mL) was added, and was then diluted with methylene chloride (150 mL), washed with water (50 mL), aqueous potassium hydrogen sulfate (1M, 50 mL) and brine (25 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was recrystallized from methylene chloride/diethyl ether to give the title compound, mp 186-187° C. (dec.).

後処理

  1. additionwas added
  2. washwashed with water (50 mL), aqueous potassium hydrogen sulfate (1M, 50 mL) and brine (25 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was recrystallized from methylene chloride/diethyl ether

出典と根拠

ORDレコード
ord-b7852c902aa6435d8264f2223b10f8b3
出典データセット
uspto-grants-2001_04
特許番号
US06218413B1

反応ノート

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