Diisopropylethylamine → (5S)-5-({[4-(4-fluorophenyl)piperidin-1-yl}sulfonyl]methyl)-5-methylimidazolidine-2,4-dione

HRID 32386ノート

反応式

HRID 32386 の反応式
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[CH3:24][C@@:25]1([CH2:32][S:33](Cl)(=[O:35])=[O:34])[C:29](=[O:30])[NH:28][C:27](=[O:31])[NH:26]1>C1COCC1>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH2:11][N:12]([S:33]([CH2:32][C@@:25]3([CH3:24])[NH:26][C:27](=[O:31])[NH:28][C:29]3=[O:30])(=[O:34])=[O:35])[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 81531Diisopropylethylamine2 回HCID 16738713(4S)-(4-methyl-2,5-dioxoimidazolidin-4-yl)methanesulphonyl chlorideHCID 218981684-(4-Fluoro-phenyl)-piperidine hydrochloride

生成物 1

HCID 59794371(5S)-5-({[4-(4-fluorophenyl)piperidin-1-yl}sulfonyl]methyl)-5-methylimidazolidine-2,4-dione

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

4-(4-Fluorophenyl)piperidine hydrochloride (63 mg, 0.29 mmol) was taken up in 3 mL of dry THF, neutralized with diisopropylethylamine (50 μL, 0.29 mmol) and cooled on an ice-water bath. [(4S)-4-metyl-2,5-dioxo-imidazolodin-4-yl]methanesulfonyl chloride (80 mg, 0.35 mmol) was added and after stirring for 10 min, diisopropylethylamine (50 μL, 0.29 mmol) was added and the reaction mixture was stirred at ambient temperature until LC-MS (APCD) indicated consumption of the amine. The reaction mixture was evaporated and the residue taken up in EtOH and heated to 50° C. and allowed to cool before water was added. The precipitated product was collected and washed with EtOH/water and dried in vacuum to yield 87 mg.

後処理

  1. temperaturecooled on an ice-water bath
  2. stirringthe reaction mixture was stirred at ambient temperature until LC-MS (APCD)
  3. customconsumption of the amine
  4. customThe reaction mixture was evaporated
  5. temperatureto cool before water
  6. additionwas added
  7. customThe precipitated product was collected
  8. washwashed with EtOH/water
  9. customdried in vacuum
  10. customto yield 87 mg

出典と根拠

ORDレコード
ord-72cdafcdd2114a89a9df74afdb6ade70
出典データセット
uspto-grants-2008_09
特許番号
US07427631B2

反応ノート

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