Dimethyl Sulfoxide → 5-({4-[(2S)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}acetyl)-4-methyl-2-benzofuran-1(3H)-one

HRID 1474404ノート

反応式

HRID 1474404 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[N:11]1([CH2:31][C@H:32]([C:34]2[CH:43]=[CH:42][C:37]3[C:38](=[O:41])[O:39][CH2:40][C:36]=3[C:35]=2[CH3:44])[OH:33])[CH2:16][CH2:15][N:14]([CH2:17][C@H:18]([C:20]2[CH:29]=[CH:28][C:23]3[C:24](=[O:27])[O:25][CH2:26][C:22]=3[C:21]=2[CH3:30])[OH:19])[CH2:13][CH2:12]1>C(Cl)Cl>[OH:19][C@@H:18]([C:20]1[CH:29]=[CH:28][C:23]2[C:24](=[O:27])[O:25][CH2:26][C:22]=2[C:21]=1[CH3:30])[CH2:17][N:14]1[CH2:13][CH2:12][N:11]([CH2:31][C:32]([C:34]2[CH:43]=[CH:42][C:37]3[C:38](=[O:41])[O:39][CH2:40][C:36]=3[C:35]=2[CH3:44])=[O:33])[CH2:16][CH2:15]1

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 595687025,5'-{piperazine-1,4-diylbis[(1S)-1-hydroxyethane-2,1-diyl]}bis(4-methyl-2-benzofuran-1(3H)-one)

生成物 1

HCID 595687295-({4-[(2S)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}acetyl)-4-methyl-2-benzofuran-1(3H)-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

To a solution of oxalyl chloride (71 uL, 0.82 mmol) in DCM (30 mL) was dropped DMSO (120 uL, 1.6 mmol) at −78° C. After stirring the mixture for 10 minutes, a DCM solution of 5,5′-{piperazine-1,4-diylbis [(1S)-1-hydroxyethane-2,1-diyl]}bis(4-methyl-2-benzofuran-1(3H)-one) (380 mg, 0.82 mmol) was added into the reaction. The reaction was stir for another 20 minutes before TEA (570 uL, 4.1 mmol) was added to the reaction mixture. The reaction was then allowed to warm up to RT slowly. TLC analysis showed two new spots right above the SM. LC analysis suggested formation of the mono-ketone as well as the di-ketone. The reaction was diluted with DCM, washed with water, dried over sodium sulfate, and purified by flash chromatography. The title product was collected after removal of solvent.

後処理

  1. additionwas added to the reaction mixture
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. custompurified by flash chromatography
  5. customThe title product was collected
  6. customafter removal of solvent

出典と根拠

ORDレコード
ord-b8e633283e2746a8979354ccaa497cae
出典データセット
uspto-grants-2015_04
特許番号
US09018211B2

反応ノート

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