Benzoic Acid → (6R,7aS)-2-(3,5-dichlorophenyl)-1,3-dioxohexahydro-1H-pyrrolo[1,2-c]imidazol-6-yl benzoate

HRID 1268762

反応式

HRID 1268762 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@H:12]3[CH2:15][C@@H:16]([OH:18])[CH2:17][N:11]3[C:10]2=[O:19])[CH:5]=[C:6]([Cl:8])[CH:7]=1.CN(C1C=CC=CN=1)C.[C:29](O)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:29]([O:18][C@H:16]1[CH2:17][N:11]2[C:10](=[O:19])[N:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)[C:13](=[O:14])[C@@H:12]2[CH2:15]1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

参加物

6

反応物 4

HCID 243Benzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 58840802(6R,7aS)-2-(3,5-dichlorophenyl)-6-hydroxytetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione

生成物 1

HCID 18446714(6R,7aS)-2-(3,5-dichlorophenyl)-1,3-dioxohexahydro-1H-pyrrolo[1,2-c]imidazol-6-yl benzoate収率 95%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (6R,7aS)-2-(3,5-dichlorophenyl)-6-hydroxytetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione (1.2 g) (4 mmol) (Preparation 6), dimethylaminopyridine (50 mg) (0.1 eq.) and benzoic acid (0.49 g) (1 eq.) in 10 mL of dry DCM at 0° C. was added DCC (0.9 g) (1 eq.) in a minimal volume of DCM. The reaction mixture was stirred to RT overnight. After filtering off the insoluble material, the reaction mixture is washed with a dilute NaHCO3 aqueous solution, with dilute HCl solution, with water, dried over MgSO4, and evaporated under reduced pressure to afford to afford the titled compound as a viscous oil (1.54 g). 1H NMR (CDCl3): 8.05 (2H,d), 7.65 (1H,m), 7.5 (1H,d), 7.43 (2H,d), 7.38 (1H,m), 5.81 (1H,t), 4.62 (1H,dd), 4.23 (1H,dd), 3.56 (1H,d), 2.68 (1H,dd), 2.05–2.20 (1H,m).

後処理

  1. filtrationAfter filtering off the insoluble material
  2. washthe reaction mixture is washed with a dilute NaHCO3 aqueous solution, with dilute HCl solution, with water
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customto afford

出典と根拠

ORDレコード
ord-ab80c39b026a40ec943039cf0f9ebf50
出典データセット
uspto-grants-2007_04
特許番号
US07199125B2

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