HRID369475

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6344

Dichloromethane

CH2Cl2

结构：CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O

HCID36314

Paclitaxel

C47H51NO14

2 次

HCID18366337

Propan-2-one--water (1/1)

C3H8O2

2 次

PRODUCTS

生成物

HCID36314

Paclitaxel

C47H51NO14

收率 65%

$结构：C/C=C(\C)C(=O)N[C@@H](c1ccccc1)[C@@H](O)C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@@H]3[C@]4(OC(C)=O)CO[C@@H]4C[C@H](O)[C@@]3(C)C(=O)[C@H](OC(C)=O)C(=C1C)C2(C)C$

HCID6436208

未命名化合物

收率 1%

PROCEDURE

实验过程

In a further embodiment of this invention, the material obtained from the acetone/water precipitation comprising at least 40% paclitaxel is further purified by conventional silica chromatography using a methylene chloride/ethylacetate elution solvent system similar to a system described in U.S. Pat. Nos. 5,618,538 and 5,480,639 to ElSohly et al. The distinctive features of the second silica chromatography step of the present invention pertain to the feed material and to the scale of operation. The feed material for the second silica chromatography column of the present invention is a large scale preparation comprising at least 40% paclitaxel obtained from the acetone/water precipitation step and typically containing 1.5-2.0 kg of solids. This material is dissolved in 5-7 L of methylene chloride and applied to a 12-in×10-ft silica gel column packed in a stainless steel pipe. Preferably a layer of Celite is added to the top of the column to prefilter the feed material. The column is eluted with a mobile phase comprising a gradient of methylene chloride to 50% methylene chloride/ethyl acetate, and fractions are collected. Fractions are pooled to obtain a heart cut with at least 65% paclitaxel and less than 1% cephalomannine with typical yields of 92%-95% of the paclitaxel present in the feed material.

WORKUP

后处理

customis further purified by conventional silica chromatography
washa methylene chloride/ethylacetate elution solvent system similar to a system
customa large scale preparation
additionPreferably a layer of Celite is added to the top of the column
washThe column is eluted with a mobile phase
customare collected

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-1bc87ab75d814ce588b9c1a00ba1ef1d
来源数据集: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06136989
来源说明: uspto-grants-2000_10

反应 SMILES

CC(C)=O.O.[CH3:6][C:7]1[C@@H:24]([O:25][C:26]([C@H:28]([OH:45])[C@@H:29]([NH:36][C:37]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:38])[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])[CH2:23][C@:19]2([OH:46])[C:20]([CH3:22])([CH3:21])[C:8]=1[C@@H:9]([O:64][C:65]([CH3:67])=[O:66])[C:10]([C@@:12]1([CH3:63])[C@H:17]([C@@H:18]2[O:47][C:48]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)=[O:49])[C@:16]2([O:58][C:59]([CH3:61])=[O:60])[CH2:56][O:57][C@@H:15]2[CH2:14][C@@H:13]1[OH:62])=[O:11].C(Cl)Cl>>[CH3:6][C:7]1[C@@H:24]([O:25][C:26]([C@H:28]([OH:45])[C@@H:29]([NH:36][C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:38])[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])[CH2:23][C@:19]2([OH:46])[C:20]([CH3:21])([CH3:22])[C:8]=1[C@@H:9]([O:64][C:65]([CH3:67])=[O:66])[C:10]([C@@:12]1([CH3:63])[C@H:17]([C@@H:18]2[O:47][C:48]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)=[O:49])[C@:16]2([O:58][C:59]([CH3:61])=[O:60])[CH2:56][O:57][C@@H:15]2[CH2:14][C@@H:13]1[OH:62])=[O:11].[CH3:43]/[CH:44]=[C:39](/[C:37]([NH:36][C@H:29]([C@@H:28]([OH:45])[C:26]([O:25][C@@H:24]1[C:7]([CH3:6])=[C:8]2[C:20]([CH3:21])([CH3:22])[C@:19]([OH:46])([C@@H:18]([O:47][C:48]([C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)=[O:49])[C@@H:17]3[C@:16]4([O:58][C:59]([CH3:61])=[O:60])[CH2:56][O:57][C@@H:15]4[CH2:14][C@H:13]([OH:62])[C@@:12]3([CH3:63])[C:10]([C@@H:9]2[O:64][C:65]([CH3:67])=[O:66])=[O:11])[CH2:23]1)=[O:27])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:38])\[CH3:40]