聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → (S)-Diethyl (7,8-Difluoro-3-Methyl-3,4-Dihydro-2H-[1,4]Benzoxazin-4-Yl)Methylene-Malonate

HRID 8478

反应方程式

HRID 8478 反应方程式
[OH-].[K+].F[C:4]1[C:26]([F:27])=[C:25]([F:28])[CH:24]=[CH:23][C:5]=1[N:6]([CH:11]=[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C@@H:7]([CH3:10])[CH2:8][OH:9].C(OC=C(C(OCC)=O)C(OCC)=O)C.O>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CN(C=O)C>[CH2:16]([O:15][C:13](=[O:14])[C:12](=[CH:11][N:6]1[C:5]2[CH:23]=[CH:24][C:25]([F:28])=[C:26]([F:27])[C:4]=2[O:9][CH2:8][C@@H:7]1[CH3:10])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:17]

参与物

7

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 6871乙氧基甲叉丙二酸二乙酯HCID 14797氢氧化钾HCID 11485652Diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate

产物 1

HCID 11089557(S)-Diethyl (7,8-Difluoro-3-Methyl-3,4-Dihydro-2H-[1,4]Benzoxazin-4-Yl)Methylene-Malonate

试剂、催化剂与溶剂 2

HCID 5963苄基三甲基氯化铵催化剂HCID 6228N,N-二甲基甲酰胺溶剂2 次

反应条件

温度
60 °C

实验过程

Potassium hydroxide (180 mg) and benzyltrimethylammonium chloride (60.7 mg) were dissolved in DMF (15 ml) by heating to 60° C. and a solution (5 ml) of diethyl [2,3,4-trifluoro[(1S)-2-hydroxy-1-methylethyl]anilino]methylenemalonate (1 g, 99.8% ee) and diethyl ethoxymethylenemalonate (120 mg) in DMF was added thereto. The obtained mixture was stirred at the same temperature for 7 hours. After adding water, the liquid reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. After evaporating the solvent, the obtained residue was subjected to silica gel column chromatography. Thus, 899 mg (99.8% ee) of the title compound was obtained as a yellow oily substance. Various spectral data was identical with those described in Japanese Patent No. 2,769,174.

后处理

  1. customthe liquid reaction mixture
  2. extractionwas extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customAfter evaporating the solvent

来源与证据

ORD记录
ord-09aad72a49c54100a1770b7ca03a3bcc
来源数据集
uspto-grants-2006_08
专利号
US07087778B2

关联笔记

加载中…