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HRID976032

反应详情

EQUATION

反应方程式

HRID 976032 的结构方程式

REACTANTS

反应物

3
结构：O=C([O-])O.[Na+]
HCID516892

Sodium Bicarbonate

CHNaO3

结构：C/C=C/[C@H]1O[C@@H]([C@@H](C)[C@H](O)[C@H](C)[C@H]2OC(=O)/C(OC)=C/C(C)=C/[C@@H](C)[C@@H](O)[C@@H](CC)[C@@H](O)[C@H](C)C/C(C)=C/C=C/[C@@H]2OC)C[C@@H](O[C@H]2C[C@@H](O)[C@H](OC(N)=O)[C@@H](C)O2)[C@@H]1C
HCID11115550

未命名化合物

结构：Cc1ccccc1S(=O)(=O)O.O
HCID12496995

未命名化合物

PRODUCTS

生成物

1
结构：C/C=C/[C@H]1O[C@@H]([C@@H](C)[C@H](O)[C@H](C)[C@H]2OC(=O)/C(OC)=C/C(C)=C/[C@@H](C)[C@@H](O)[C@@H](CC)[C@@H](O)[C@H](C)C/C(C)=C/C=C/[C@@H]2OC)C[C@@H](O)[C@@H]1C
HCID11072454

未命名化合物

收率 32.8%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CC#N.O
溶剂HCID18373917

Acetonitrile--water (1/1)

C2H5NO

CONDITIONS

反应条件

温度
38 °C

PROCEDURE

实验过程

350 mg (1.83 mmol, 3 equiv.) of toluenesulfonic acid monohydrate (recrystallised from CHCl3) are added to a solution of 467 mg of 21-deoxyconcanamycin A (0.55 mmol) in 55 ml of CH3CN/H2O (5:1) and the reaction mixture is stirred at 38° C. for 12 hours. For working-up, the reaction mixture is cooled to 0° C. and 50 ml of saturated NaHCO3 solution are added; the organic solvent is removed in vacuo and the aqueous phase is extracted with CHCl3. TLC monitoring on silica gel (eluant: EtOAc/hexane 1:1) revealed two new zones in addition to the starting material at the starting spot. Column chromatography on silica gel (gradient EtOAc/hexane, 1:1 EtOAc) yields 63 mg (22% of the conversion) of 16-demethyl-21-deoxyconcanolide A, 122 mg of 21-deoxyconcanolide A (42% of the conversion) and 105 mg of starting material.

WORKUP

后处理

  1. temperaturethe reaction mixture is cooled to 0° C.
  2. customthe organic solvent is removed in vacuo
  3. extractionthe aqueous phase is extracted with CHCl3
  4. additionin addition to the starting material at the starting spot