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

HRID 49964

Reaction equation

HRID 49964 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-db45c962de67409eab1be90e37d7b657
Source dataset
uspto-grants-2004_03
Patent number
US06710064B2

Linked notes

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