聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → (7aS,6S)-2-(3,5-dichloro-phenyl)-6-(4-bromophenoxy)-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione

HRID 49982

反应方程式

HRID 49982 反应方程式
CO[C:3](=[O:17])[C@@H:4]1[CH2:8][C@H:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)[CH2:6][NH:5]1.C([O-])([O-])=O.[K+].[K+].[Cl:24][C:25]1[CH:26]=[C:27]([N:32]=[C:33]=[O:34])[CH:28]=[C:29]([Cl:31])[CH:30]=1.O>CN(C=O)C>[Cl:24][C:25]1[CH:26]=[C:27]([N:32]2[C:3](=[O:17])[C@@H:4]3[CH2:8][C@H:7]([O:9][C:10]4[CH:11]=[CH:12][C:13]([Br:16])=[CH:14][CH:15]=4)[CH2:6][N:5]3[C:33]2=[O:34])[CH:28]=[C:29]([Cl:31])[CH:30]=1

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 11430碳酸钾HCID 944603,5-二氯苯异氰酸酯HCID 26192761Methyl (2S,4S)-4-(4-bromophenoxy)-2-pyrrolidinecarboxylate

产物 1

HCID 9804074(7aS,6S)-2-(3,5-dichloro-phenyl)-6-(4-bromophenoxy)-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
20 °C

实验过程

The compound of formula (II), wherein R11 is 4-bromo, m is 0, W=O, and the bonds depicted as wavy bonds define the 7aS,6S stereoisomer, was prepared as follows. To a solution of cis-4-(4-bromo-phenoxy)-L-proline methyl ester (0.2 g) (0.66 mmol) (Preparation 4) and K2CO3 (0.09 g) (1 eq.) in 10 mL of DMF at 0° C. was added 3,5-dichlorophenyl isocyanate (0.12 g) (1 eq.). The reaction mixture was allowed to warm to 20° C. and was stirred overnight. After adding water, the mixture was extracted with EtOAc. The combined organic extracts were washed with water, dried over MgSO4, and evaporated under reduced pressure to afford after SiO2 chromatography (eluent: DCM), the above-titled compound (60 mg). Mp=116° C. NMR (DMSO, 200 MHz): 7.75 (1H, m), 7.5-7.4 (4H, d+d), 6.85 (2H, d), 5.1 (1H, m), 4.6 (1H, dd), 3.95 (1H, dd), 3.35 (1H, dd), 2.7-2.5 (1H, m), 2.25 (1H, bd).

后处理

  1. customwas prepared
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customto afford after SiO2 chromatography (eluent: DCM)

来源与证据

ORD记录
ord-d08659727858425597f2d5fe8444c906
来源数据集
uspto-grants-2004_03
专利号
US06710064B2

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