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 1187147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1187147
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

Komponenten

5

Edukt 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)

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6652f94c9fa148f09815e58bb41304c9
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673920B2

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