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HRID1682247

反应详情

EQUATION

反应方程式

HRID 1682247 的结构方程式

REACTANTS

反应物

3
结构：O=P(O)(O)O
HCID1004

Phosphoric acid

H3O4P

结构：[Na+].[OH-]
HCID14798

Sodium Hydroxide

HNaO

结构：COc1c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc2c(c1OC)-c1ccc(OC)c(=O)cc1[C@@H](NC(C)=O)CC2
HCID92763

Colchicoside

C27H33NO11

PRODUCTS

生成物

1
结构：COc1c(O)cc2c(c1OC)-c1ccc(OC)c(=O)cc1[C@@H](NC(C)=O)CC2
HCID299664

3-Desmethylcolchicine

C21H23NO6

收率 102.3%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：O
溶剂HCID962

Water

H2O

CONDITIONS

反应条件

温度
25 °C

PROCEDURE

实验过程

A mixture of 250 mg of colchicoside and 2 ml of 85-86% H3PO4 is stirred at 25° C. for 24 hours. The yellow solution is diluted with 10 ml of water, adjusted to pH 5 by addition of 2N NaOH and extracted with methylene chloride. The extracts are dried (Na2SO4), evaporated and chromatographed on Al2O3 (basic, Alfa Division, CH2C12 /MeOH=95:5). The appropriate fractions after evaporation of solvent and crystallization from acetone afford 180 mg (89%) of 3-demethylcolchicine: mp 176°-177° C. (resolidification at 205°-210° C. and 2nd mp 270° C. (dec.), [α]D =-151° (solvate crystal, CHCl3).

WORKUP

后处理

  1. extractionextracted with methylene chloride
  2. dry with materialThe extracts are dried (Na2SO4)
  3. customevaporated
  4. customchromatographed on Al2O3 (basic, Alfa Division, CH2C12 /MeOH=95:5)
  5. customThe appropriate fractions after evaporation of solvent and crystallization from acetone