Dimethyl Sulfoxide → HCID 71143526、化合物

HRID 571457ノート

反応式

HRID 571457 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]1[CH2:15][N:14]([C:16]2[CH:27]=[CH:26][C:19]([C:20]([NH:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[CH:18][CH:17]=2)[CH2:13]1.C(N(CC)CC)C>>[CH:23]([NH:22][C:20](=[O:21])[C:19]1[CH:18]=[CH:17][C:16]([N:14]2[CH2:13][C:12](=[O:11])[CH2:15]2)=[CH:27][CH:26]=1)([CH3:25])[CH3:24]

参加物

5

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 711435344-(3-Hydroxy-1-azetidinyl)-N-(1-methylethyl)benzamide

生成物 1

HCID 71143526HCID 71143526、化合物収率 77.4%

反応条件

温度
-78 °C

実験手順

To a cooled (−78° C.) solution of oxalyl chloride (1.05 mL, 12.4 mmol) in dichloromethylene (20 mL) was added dropwise dimethyl sulfoxide (1.71 mL, 24.1 mmol). The mixture was stirred at −78° C. for 10 minutes. Then a suspension of 4-(3-hydroxyazetidin-1-yl)-N-isopropylbenzamide (1.72 g, 7.34 mmol) in dichloromethylene (20 mL) was added. The mixture was stirred at −78° C. for 1 hour, and then triethylamine (7.04 mL, 50.5 mmol) was added. The mixture was stirred at −78° C. for an additional 1.5 hour. The mixture was washed with aq. NaHCO3 and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The precipitates were washed with ether and collected by filtration to afford the desired product (1.32 g, 77%) which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=233.1.

後処理

  1. additionwas added
  2. stirringThe mixture was stirred at −78° C. for 1 hour
  3. stirringThe mixture was stirred at −78° C. for an additional 1.5 hour
  4. washThe mixture was washed with aq. NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washThe precipitates were washed with ether
  9. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-6cc51edfa181403e8127e9165d9c935a
出典データセット
uspto-grants-2015_05
特許番号
US09023840B2

反応ノート

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