HRID551520

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6344

Dichloromethane

CH2Cl2

HCID6775

2,3-Dichloro-5,6-dicyano-p-benzoquinone

C8Cl2N2O2

$结构：CCNC(=O)CCC/C=C\C[C@@H]1[C@@H](/C=C/[C@@H](O)CCc2ccccc2)[C@H](O)C[C@@H]1O$

HCID5311027

Bimatoprost

C25H37NO4

PRODUCTS

生成物

$结构：CCNC(=O)CCC/C=C\C[C@@H]1[C@@H](/C=C/C(=O)CCc2ccccc2)[C@H](O)C[C@@H]1O$

HCID35028392

(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E)-3-oxo-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamide

C25H35NO4

收率 63.5%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度: 40 °C

PROCEDURE

实验过程

A mixture of bimatoprost 1 (0.33 g, 0.8 mmol), DDQ (0.68 g, 3.0 mmol), CH2Cl2 (5 mL) and 1,4-dioxane (5 mL) was stirred for 24 h at 40° C. and evaporated in vacuo. The residue was purified by chromatography on a silica gel (20 g, eluent EtOAc then EtOAc/MeOH 20:1) to give 0.21 g (63%) of 15-keto bimatoprost 1c as yellow oil.

WORKUP

后处理

customevaporated in vacuo
customThe residue was purified by chromatography on a silica gel (20 g, eluent EtOAc