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HRID1271532

反应详情

EQUATION

反应方程式

HRID 1271532 的结构方程式

REACTANTS

反应物

4
结构：CC(C)=O
HCID180

Acetone

C3H6O

结构：O=C(O)CC(O)(CC(=O)O)C(=O)O
HCID311

Citric acid

C6H8O7

结构：N=O
HCID945

Nitroxyl

HNO

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)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O
HCID447043

Azithromycin

C38H72N2O12

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@@H](C)CN[C@H](C)[C@@H](O)[C@]1(C)O
HCID9810601

2-Ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-15-oxo-11-{[3,4,6-trideoxy-3-(dimethylamino)hexopyranosyl]oxy}-1-oxa-6-azacyclopentadecan-13-yl 2,6-dideoxy-3-C-methyl-3-O-methylhexopyranoside

C37H70N2O12

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CO
溶剂HCID887

Methanol

CH4O

结构：[BH4-].[Na+]
溶剂HCID4311764

Sodium borohydride (Na(BH4))

H4BNa

PROCEDURE

实验过程

In accordance with one aspect of the present invention, there is provided a method of preparing azithromycin of formula (I) comprising the steps of: (a) reducing 6,9-imino ether of formula (III) dissolved in methanol with 5 to 7 mole equivalents of NaBH4 at −20 to −10° C., treating the reaction mixture with an acidic aqueous acetone solution of citric acid, and adjusting the solution pH to 10.5 to 12.0 to obtain a crystalline hydrate of 9-deoxo-9a-aza-9a-homoerythromycin A of formula (II); and

WORKUP

后处理

  1. customIn accordance with one aspect of the present invention, there is provided