Potassium Carbonate → (7aS,6S)-2-(3,5-dichloro-phenyl)-6-hydroxy-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione

HRID 49965

反応式

HRID 49965 の反応式
CO[C:3](=[O:10])[C@@H:4]1[CH2:8][C@H:7]([OH:9])[CH2:6][NH:5]1.C([O-])([O-])=O.[K+].[K+].[Cl:17][C:18]1[CH:19]=[C:20]([N:25]=[C:26]=[O:27])[CH:21]=[C:22]([Cl:24])[CH:23]=1>CN(C=O)C>[Cl:17][C:18]1[CH:19]=[C:20]([N:25]2[C:3](=[O:10])[C@@H:4]3[CH2:8][C@H:7]([OH:9])[CH2:6][N:5]3[C:26]2=[O:27])[CH:21]=[C:22]([Cl:24])[CH:23]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 944603,5-Dichlorophenyl isocyanateHCID 7021050methyl (2S,4S)-4-hydroxypyrrolidine-2-carboxylate

生成物 1

HCID 12096649(7aS,6S)-2-(3,5-dichloro-phenyl)-6-hydroxy-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione収率 23.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of cis-4-hydroxy-L-proline methyl ester (0.53 g) (0.0036 mol) in 10 mL of DMF cooled at 0° C. was added K2CO3 (0.52 g) (1.1 eq.), then 3,5-dichlorophenyl isocyanate (0.75 g) (1.1 eq.). The reaction was stirred overnight at RT and the insoluble material removed by filtration. The solution was concentrated under vacuum and the residue dissolved in DCM. 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-95/5) to afford the titled compound as a white solid (0.25 g). NMR (CDCl3, 200 MHz): 7.35 (3H, s), 4.45 (1H, m), 4.30 (1H, dd), 4.0 (1H, d), 3.1 (1H, dd), 2.35-2.2 (2H, m), 1.95 (1H, bs, OH).

後処理

  1. customthe insoluble material removed by filtration
  2. concentrationThe solution was concentrated under vacuum
  3. dissolutionthe residue dissolved in DCM
  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-95/5)

出典と根拠

ORDレコード
ord-4c8d7628b5954f35b54cdaa39e5ad743
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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