Sodium hydride → HCID 22730180, Verbindung

HRID 2085812Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2085812
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.C1OCCOCCOCCOCCOC1.[H-].[Na+].Br[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43]([C:46]([O:48][CH3:49])=[O:47])=[CH:42][CH:41]=2)=[C:36]([O:50][CH3:51])[CH:35]=1>CN(C=O)C.O>[CH3:51][O:50][C:36]1[CH:35]=[C:34]([CH2:33][N:7]2[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3][C:2]2=[O:1])[CH:39]=[CH:38][C:37]=1[C:40]1[CH:45]=[CH:44][C:43]([C:46]([O:48][CH3:49])=[O:47])=[CH:42][CH:41]=1

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 22730382HCID 22730382, Verbindung

Produkt 1

HCID 22730180HCID 22730180, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of Example 500B (328 mg, 1.64 mmol) in DMF (4 mL) at room temperature was treated with 15-crown-5 (361 mg, 1.64 mmol) and 60% sodium hydride in mineral oil (66 mg, 1.64 mmol). The mixture was treated with a solution of Example 500C (500 mg, 1.49 mmol) in DMF (2 mL), heated to 60° C. for 16 hours, cooled to room temperature, treated with water (20 mL), and extracted three times with ethyl acetate (50 mL). The combined extracts were washed with brine (10 mL), dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 1:1 ethyl acetate/hexanes to provide the desired product.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionextracted three times with ethyl acetate (50 mL)
  3. washThe combined extracts were washed with brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 1:1 ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-bd5e41573ccf4613a390af4ad1b836b8
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06720338B2

Notizen zur Reaktion

Wird geladen…