海萝胶 → 4-噻唑羧酸叔丁酯

HRID 539652

反应方程式

HRID 539652 反应方程式
[S:1]1[CH:5]=[C:4]([C:6]([OH:8])=[O:7])[N:3]=[CH:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:21](O)([CH3:24])([CH3:23])[CH3:22].C1CCN2C(=NCCC2)CC1.Cl>CN(C=O)C.O>[S:1]1[CH:5]=[C:4]([C:6]([O:8][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:7])[N:3]=[CH:2]1

参与物

8

反应物 5

HCID 313海萝胶HCID 6386叔丁醇HCID 68263N,N'-羰基二咪唑HCID 81184DBUHCID 304271噻唑-4-甲酸

产物 1

HCID 167442944-噻唑羧酸叔丁酯收率 47%

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
60 °C

实验过程

To a solution of thiazole-4-carboxylic acid 7.1 (1 g, 7.2 mmol) and carbonyldiimidazole (6.3 g, 38.7 mmol) in commercial dry DMF (50 mL) under N2 was stirred at 50° C. for 20 min. Tert-butanol (8.6 g, 116.0 mmol) and DBU (5.8 mL, 38.7 mmol) were then successively added at once and the reaction was warmed at 60° C. for 48 h. The RM was then allowed to cool down to RT and the pH was adjusted to 4 with a solution of HCl (2M, ˜80 mL). The mixture was diluted with water (250 mL) and extracted with Et2O (3×100 mL). The combined org. layers were washed with brine (250 mL), dried over MgSO4, concentrated and purified on silica gel using DCM to afford title product as yellowish oil (47%). Yield: 3.37 g (47%). LCMS: P=98%, rt=3.65 nm, m/z=186.

后处理

  1. temperatureto cool down to RT
  2. extractionextracted with Et2O (3×100 mL)
  3. washlayers were washed with brine (250 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified on silica gel

来源与证据

ORD记录
ord-beb5a80539924462b21bb4ef310f3bf3
来源数据集
uspto-grants-2014_10
专利号
US08871761B2

关联笔记

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