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

HRID 1268761

반응식

HRID 1268761 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

HCID 58840802(6R,7aS)-2-(3,5-dichlorophenyl)-6-hydroxytetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione수율 50.6%

실험 절차

(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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0c20a3d524a340e4ad8e4a34ced260e2
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199125B2

연결된 노트

불러오는 중…