Sodium hydride → 2,2-dimethylpropyl 4-(4-[5-[(1S)-1-hydroxyethyl]-1,2,4-oxadiazol-3-yl]pyridin-2-yl)-1-piperazinecarboxylate

HRID 421822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 421822
[NH2:1][C:2](=[N:23][OH:24])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]2)[CH:4]=1.[H-].[Na+].[C:27](OC)(=O)[C@H:28]([CH3:30])[OH:29].[Cl-].[NH4+]>O1CCCC1>[OH:29][C@H:28]([C:30]1[O:24][N:23]=[C:2]([C:3]2[CH:8]=[CH:7][N:6]=[C:5]([N:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:16])[CH2:11][CH2:10]3)[CH:4]=2)[N:1]=1)[CH3:27]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 94386methyl (S)-lactateHCID 1363817182,2-Dimethylpropyl 4-{4-[amino(hydroxyimino)methyl]pyridin-2-yl}-1-piperazinecarboxylate

Produkt 1

HCID 119927032,2-dimethylpropyl 4-(4-[5-[(1S)-1-hydroxyethyl]-1,2,4-oxadiazol-3-yl]pyridin-2-yl)-1-piperazinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2,2-Dimethylpropyl 4-{4-[amino(hydroxyimino)methyl]pyridin-2-yl}-1-piperazinecarboxylate (657 mg) was dissolved in tetrahydrofuran (10 mL), oily sodium hydride (82.6 mg) was added thereto and stirred at 60° C. for 15 minutes, then methyl (S)-lactate (0.333 mL) was added thereto and heated under reflux for 1 hour. Aqueous saturated ammonium chloride solution was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain 402 mg of the entitled compound as a colorless solid.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was evaporated away
  7. customthe resulting residue was isolated
  8. custompurified through silica gel column chromatography (hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-1c7c403979834b1bba20428783564d99
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101618B2

Notizen zur Reaktion

Wird geladen…