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HRID2226987

反应详情

EQUATION

反应方程式

HRID 2226987 的结构方程式

REACTANTS

反应物

3
结构：[K+].[OH-]
HCID14797

Potassium hydroxide

HKO

2 次

结构：CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(OC)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
HCID84029

Clarithromycin

C38H69NO13

结构：CCOCCOCCOCCOC(=O)Cl
HCID18964125

2-[2-(2-Ethoxyethoxy)ethoxy]ethyl carbonochloridate

C9H17ClO5

2 次

PRODUCTS

生成物

2
结构：CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
HCID12560

Erythromycin

C37H67NO13

结构：CCOCCOCCOCCOC(=O)[O-]
HCID131718681

未命名化合物

收率 598.4%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：C1CCOC1
溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

To a solution of 6-O-methylerythromycin A (10 g) in tetrahydrofuran (50 ml ), were added 95 % potassium hydroxide powder (0.87 g ) and 2 - [2 - (2 -ethoxyethoxy ) ethoxy ]ethyl chloroformate (3.60 g) under ice-cooling. After stirring for 3 hours, 95% potassium hydroxide powder (0.24 g ) and 2- [2-(2 -ethoxyethoxy ) ethoxy ]ethyl chloroformate (0.98 g ) were further added thereto and the mixture was stirred for additional 2 days. The post treatment was performed by the same method as the one described in Example 7. The crude product thus obtained was purified by silica gel column chromatography (elution solvent; acetone : n-hexane =7 : 13 - 2 : 3) and then crystallized from chloroform/n-hexane. Thus 6-0-methylerythromycin A 2 '- {2- [2- (2-ethoxyethoxy ) ethoxy]ethyl}carbonate (8.85 g) was obtained as a white powder.

WORKUP

后处理

  1. temperaturecooling
  2. stirringthe mixture was stirred for additional 2 days
  3. customThe crude product thus obtained
  4. customwas purified by silica gel column chromatography (elution solvent; acetone : n-hexane =7 : 13 - 2 : 3)
  5. customcrystallized from chloroform/n-hexane