Hydrochloric Acid → (6R,7aS)-2-(3,5-dichlorophenyl)-6-hydroxytetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione

HRID 1268761

Reaktionsgleichung

Reaktionsgleichung von HRID 1268761
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:19][C@H:18]([OH:20])[CH2:17][C@H:13]2[C:14](O)=[O:15])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:14](=[O:15])[C@@H:13]3[CH2:17][C@@H:18]([OH:20])[CH2:19][N:12]3[C:10]2=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Komponenten

3

Edukt 2

HCID 313Hydrochloric AcidHCID 60073589(4R)-1-{[(3,5-dichlorophenyl)amino]carbonyl}-4-hydroxy-L-proline

Produkt 1

HCID 58840802(6R,7aS)-2-(3,5-dichlorophenyl)-6-hydroxytetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dioneAusbeute 50,6 %

Versuchsvorschrift

(4R)-1-{[(3,5-dichlorophenyl)amino]carbonyl}-4-hydroxy-L-proline (6.8 g) (0.021 mol) (Preparation 5) was combined with 35 mL of 1N HCl and refluxed for 11 hrs. The organic oil was separated from the reaction mixture and dissolved in EtOAc. The organic layer was washed with water, dried over MgSO4, and evaporated under reduced pressure. The resulting residue was purified on a SiO2 column (eluent: DCM/acetone-90/10) to afford the titled compound as a white solid (3.2 g). 1H NMR (CDCl3): 7.4 (2H,d), 7.35 (1H,m), 4.8 (1H,m), 4.60 (1H,dd), 3.98 (1H,dd), 3.35 (1H,d), 2.39 (1H,dd), 2.05 (1H,d,OH), 1.80–1.95 (1H,m).

Aufarbeitung

  1. temperaturerefluxed for 11 hrs
  2. customThe organic oil was separated from the reaction mixture
  3. dissolutiondissolved in EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure
  7. customThe resulting residue was purified on a SiO2 column (eluent: DCM/acetone-90/10)

Quellen und Nachweise

ORD-Eintrag
ord-0c20a3d524a340e4ad8e4a34ced260e2
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199125B2

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