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Acetic Acid → 4-[4-(Diethoxyphosphorylmethylsulfonyl)piperazin-1-yl]-2-methyl-quinoline

HRID 333933
ノート
印刷プレビュー

反応式

HRID 333933 の反応式
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:32]([O:34][P:35](Cl)([O:37][CH2:38][CH3:39])=[O:36])[CH3:33].C(O)(=O)C>C1COCC1.O>[CH2:32]([O:34][P:35]([CH2:21][S:18]([N:15]1[CH2:14][CH2:13][N:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([CH3:1])[CH:11]=2)[CH2:17][CH2:16]1)(=[O:20])=[O:19])([O:37][CH2:38][CH3:39])=[O:36])[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 176Acetic AcidHCID 13139Diethyl chlorophosphateHCID 2733832Lithium hexamethyldisilazaneHCID 668358192-Methyl-4-(4-methylsulfonylpiperazin-1-yl)quinoline

生成物 1

HCID 866915914-[4-(Diethoxyphosphorylmethylsulfonyl)piperazin-1-yl]-2-methyl-quinoline収率 97.5%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

2-Methyl-4-(4-methylsulfonylpiperazin-1-yl)quinoline (70 mg, 0.23 mmol) was placed in a Schlenk tube under an argon atmosphere, anhydrous THF (1.5 ml) was added and the solution cooled to −78° C. Lithium hexamethyldisilazid (50.6 mmol, 50.6 μl of a 1M solution in anhydrous THF) was added dropwise and the mixture stirred for one hour at −78° C. Diethylchlorophosphate (33.3 μl, 0.23 mmol) was added dropwise and stirring was continued for one hour. Acetic acid (100 μl) and water (1.5 ml) were added, the temperature raised slowly to room temperature and the mixture was extracted with diethylether (3×). The combined organic phases were washed with water and brine and evaporated to dryness under reduced pressure. 99 mg of an oily residue were obtained (0.22 mmol, 98%). MS (APCI) m/z=441.7 [M+1]+.

後処理

  1. stirringstirring
  2. waitwas continued for one hour
  3. temperaturethe temperature raised slowly to room temperature
  4. extractionthe mixture was extracted with diethylether (3×)
  5. washThe combined organic phases were washed with water and brine
  6. customevaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-aabd939b1fc54fb99154219a2c342035
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08883791B2

反応ノート

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