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(2R,5R)-2,5-dimethylpiperazine → N,N-diethyl-4-(3-hydroxy-alpha-((2R, 5R)-2,5-dimethyl-1-piperazinyl)benzyl)-benzamide

HRID 1460087
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1460087
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([CH:11](Cl)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][Si](C(C)(C)C)(C)C)[CH:13]=2)=[CH:7][CH:6]=1)[CH3:2].[CH3:30][C@@H:31]1[CH2:36][NH:35][C@H:34]([CH3:37])[CH2:33][NH:32]1.N[C@@H](C(N[C@@H](C(O)=O)C)=O)C.O=C1NCCNC1=O.O.[F-].C([N+](CC)(CC)CC)C>C(#N)C>[CH2:28]([N:3]([CH2:1][CH3:2])[C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([N:32]2[CH2:33][C@@H:34]([CH3:37])[NH:35][CH2:36][C@H:31]2[CH3:30])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)=[CH:7][CH:6]=1)[CH3:29]
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Komponenten

6

Edukt 4

HCID 7057916(2R,5R)-2,5-dimethylpiperazineHCID 16211652Tetraethylammonium fluoride hydrateHCID 223500364-(3-(tert-butyldimethylsilyloxy)-alpha-chlorobenzyl)-N,N-diethylbenzamideHCID 131721055D-Ala-D-Ala diketopiperazine

Produkt 1

HCID 54198546N,N-diethyl-4-(3-hydroxy-alpha-((2R, 5R)-2,5-dimethyl-1-piperazinyl)benzyl)-benzamide
Ausbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

The procedure described in Example 12 was followed with 11.62 g (27 mmol) of N,N-diethyl-4-(3-(tert-butyldimethylsilyloxy)-α-chlorobenzyl) benzamide, prepared as in Example 11, and 9.42 g (82 mmol) of (-)-(2R,5R)-2,5-dimethylpiperazine, prepared from D-Ala-D-Ala-diketopiperazine (Bachem Chemicals, Philadelphia, Pa.) as described by Jung and Rohloff (J. Org. Chem. 50, 4909-13(1985)). The crude product was dissolved in 100 mL of acetonitrile and 8.07 g (40 mmol) of tetraethylammonium fluoride hydrate was added. The solution was stirred at room temperature overnight. The solvent was evaporated, and the residue was treated with 100 mL of aqueous 1N hydrochloric acid and extracted with 200 mL of diethyl ether. The aqueous layer was adjusted to pH 8 with aqueous 5M sodium hydroxide, and extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, and evaporated to give 8.03 g (75%) of N,N-diethyl-4-(3-hydroxy-α-((2R, 5R)-2,5-dimethyl-1-piperazinyl)benzyl)-benzamide as a light brown solid.

Aufarbeitung

  1. customThe solvent was evaporated
  2. additionthe residue was treated with 100 mL of aqueous 1N hydrochloric acid
  3. extractionextracted with 200 mL of diethyl ether
  4. extractionextracted with dichloromethane
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9b50ffd9edf844019d7b2b7401575e65
Quelldatensatz
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05854249

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