碳酸氢钠 → HCID 21356561，化合物

HRID 8158

反应方程式

HRID 8158 反应方程式
C(O[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([N:19]2[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]2)=[C:16]([F:18])[CH:17]=1)=O)C1C=CC=CC=1.C([Li])CCC.[CH2:30]([O:34][C:35](=[O:39])CCC)[C@@H:31]1[O:33]C1.C(=O)(O)[O-].[Na+]>O1CCCC1.CN1CCCN(C)C1=O.C(OCC)(=O)C>[F:18][C:16]1[CH:17]=[C:12]([N:11]2[CH2:9][C@H:30]([CH2:31][OH:33])[O:34][C:35]2=[O:39])[CH:13]=[CH:14][C:15]=1[N:19]1[CH:23]=[C:22]([CH3:24])[N:21]=[CH:20]1

参与物

8

反应物 4

HCID 516892碳酸氢钠HCID 2724536缩水甘油丁酸酯HCID 218766725-Benzyloxycarbonylamino-2-(4-methylimidazol-1-yl)fluorobenzeneHCID 178418339正丁基锂

产物 1

HCID 21356561HCID 21356561，化合物收率 33.7%

试剂、催化剂与溶剂 3

HCID 8028四氢呋喃溶剂2 次HCID 8857乙酸乙酯溶剂HCID 81646N,N-二甲基丙烯基脲溶剂

实验过程

5-Benzyloxycarbonylamino-2-(4-methylimidazol-1-yl)fluorobenzene (54 g, 0.166 M) was dissolved in a mixture of dry tetrahydrofuran (600 ml) and 1,3-dimethyl-2,4,5,6-tetrahydro-2(1H)-pyrimidinone (100 ml) under nitrogen, cooled to −70°, and treated with a solution of n-butyllithium (1.6 M in isohexane, 114 ml), over 30 minutes. After stirring for 30 minutes at 25–70°, a solution of (R)-glycidylbutyrate (26.35 g, 0.183 M) in dry tetrahydrofuran (50 ml) was added over 15 minutes. Stirring was continued for 16 hours allowing the temperature to rise to ambient. The mixture was treated with aqueous sodium bicarbonate (5%, 500 ml) and ethyl acetate (800 ml), and undissolved solid was removed and washed well with diethyl ether to give title product (16.3 g).

后处理

  1. temperaturecooled to −70°
  2. stirringStirring
  3. waitwas continued for 16 hours
  4. customwas removed
  5. washwashed well with diethyl ether

来源与证据

ORD记录
ord-d11bd3e8708b472f9e50678f20eb8f7e
来源数据集
uspto-grants-2006_08
专利号
US07087629B2

关联笔记

加载中…