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HRID742176

反应详情

EQUATION

反应方程式

HRID 742176 的结构方程式

REACTANTS

反应物

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：O=S(=O)(c1ccccc1)N(F)S(=O)(=O)c1ccccc1
HCID588007

N-Fluorobenzenesulfonimide

C12H10FNO4S2

PRODUCTS

生成物

1
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@](C)(F)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O
HCID71260

Flurithromycin

C37H66FNO13

收率 82.2%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CC(=O)O
溶剂HCID176

Acetic Acid

C2H4O2

PROCEDURE

实验过程

Erythromycin A (3 g, 4.1 mmole) was dissolved in glacial acetic acid (12 mL) at room temperature and stirred for 2 hours. N-fluorobenzenesulfonimide (1.6 g, 4.1 mmole) was added and stirring continued for an additional 4 hours at 22° C. The reaction was worked-up in the same manner as Example 1 to afford 2.533 g of crude flurithromycin. This material was recrystallized as described in Example 1 to yield 0.8 g (26% yield) of flurithromycin. This example shows the embodiment of the invention where the anydro derivative of erythromycin is prepared as an unisolated reaction intermediate and the N-F fluorination reaction is carried out without a buffer.

WORKUP

后处理

  1. stirringstirring
  2. waitcontinued for an additional 4 hours at 22° C