Chloroform → (S)-t-Butyl 2-(3-((3,4-dimethoxyphenoxy)methyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboxylate

HRID 710049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710049
C(Cl)(Cl)Cl.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[O:10][CH2:11][C:12](=[N:14][OH:15])[NH2:13].[C:21]([O:25][C:26]([N:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[C:33](O)=O)=[O:27])([CH3:24])([CH3:23])[CH3:22].CCN=C=NCCCN(C)C.Cl>O>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[O:10][CH2:11][C:12]1[N:13]=[C:33]([C@@H:29]2[CH2:30][CH2:31][CH2:32][N:28]2[C:26]([O:25][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:27])[O:15][N:14]=1

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 867067612-(3,4-Dimethoxyphenoxy)-N'-hydroxyacetoimidamide

Produkt 1

HCID 86706762(S)-t-Butyl 2-(3-((3,4-dimethoxyphenoxy)methyl)-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboxylateAusbeute 10,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a CHCl3 (20 ml) solution of the compound (1.0 g) obtained in Example 12-(1) and (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (1.0 g), WSC.HCl (1.0 g) was added and the mixture was stirred at room temperature for 4 hours. Water was added, followed by extraction with CHCl3. After distilling off the solvent under reduced pressure, the residue was dissolved in toluene (20 ml), followed by refluxing for 2 hours. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (190 mg).

Aufarbeitung

  1. extractionfollowed by extraction with CHCl3
  2. distillationAfter distilling off the solvent under reduced pressure
  3. dissolutionthe residue was dissolved in toluene (20 ml)
  4. temperatureby refluxing for 2 hours
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel chromatography (AcOEt/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c6ddbeae3619443382fac0b2f0710606
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181229B2

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