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

HRID 49964

反応式

HRID 49964 の反応式
[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

参加物

3

反応物 2

HCID 313Hydrochloric AcidHCID 611847551-(3,5-dichloro-phenylcarbamoyl)-4-hydroxy-L-proline

生成物 1

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

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-db45c962de67409eab1be90e37d7b657
出典データセット
uspto-grants-2004_03
特許番号
US06710064B2

関連ノート

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