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

HRID 49964

반응식

HRID 49964 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:19][CH: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 611847551-(3,5-dichloro-phenylcarbamoyl)-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

1-(3,5-dichloro-phenylcarbamoyl)-4-hydroxy-L-proline (6.8 g) (0.021 mol) (Preparation 1) was combined with 35 mL of 1 N 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). NMR (CDCl3, 200 MHz): 7.4 (2H, d), 7.35 (1H, m), 4.75 (1H, m), 4.60 (1H, dd), 3.95 (1H, dd), 3.35 (1H, d), 2.75 (1H, m, OH), 2.40 (1H, dd), 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-db45c962de67409eab1be90e37d7b657
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710064B2

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