HRID345972

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID1123

l-Taurine

C2H7NO3S

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](OC(=O)CCC(=O)O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O

HCID25024567

Paclitaxel succinate

C51H55NO17

PRODUCTS

生成物

HCID7922

Succinic anhydride

C4H4O3

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

HCID25024567

Paclitaxel succinate

C51H55NO17

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID1049

Pyridine

C5H5N

PROCEDURE

实验过程

2'-{[4-((2-sulfoethyl)amino)-1,4-dioxobutyl]oxy}taxol sodium salt and 2'-{[4-((3-sulfopropyl)amino-1,4-dioxobutyl]-oxy}taxol sodium salt were produced in high yield by coupling 2'-succinyltaxol with taurine (2-aminoethyl sulfonic acid) and 3-aminopropyl sulfonic acid tetrabutylammonium salts, respectively. Note that other quaternary ammonium salts may be used to make the aminoalkyl sulfonic acids organic solvent soluble. 2'-succinyltaxol was formed by the reaction of succinic anhydride with taxol for two hours at room temperature in pyridine or DMP. In comparison with the NMR spectrum of taxol, the NMR spectrum of 2'-succinyltaxol showed a downfield shift of the C-2' proton signal to 5.51 ppm, and the succinyl proton caused multiplets centered about 2.6 ppm.

WORKUP

后处理

customin high yield

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-f1b9b1b1b7414784b308a6e5af160e9b
来源数据集: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05059699
来源说明: uspto-grants-1991_10

反应 SMILES

[CH3:1][C:2]1[C@@H:19]([O:20][C:21]([C@H:23]([O:40][C:41]([CH2:43][CH2:44][C:45]([OH:47])=[O:46])=[O:42])[C@@H:24]([NH:31][C:32]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:33])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:18][C@:14]2([OH:48])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([O:66][C:67]([CH3:69])=[O:68])[C:5]([C@@:7]1([CH3:65])[C@H:12]([C@@H:13]2[O:49][C:50]([C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)=[O:51])[C@:11]2([O:60][C:61]([CH3:63])=[O:62])[CH2:58][O:59][C@@H:10]2[CH2:9][C@@H:8]1[OH:64])=[O:6].NCCS(O)(=O)=O>N1C=CC=CC=1>[CH3:1][C:2]1[C@@H:19]([O:20][C:21]([C@H:23]([O:40][C:41]([CH2:43][CH2:44][C:45]([OH:47])=[O:46])=[O:42])[C@@H:24]([NH:31][C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:33])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:18][C@:14]2([OH:48])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([O:66][C:67]([CH3:69])=[O:68])[C:5]([C@@:7]1([CH3:65])[C@H:12]([C@@H:13]2[O:49][C:50]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[O:51])[C@:11]2([O:60][C:61]([CH3:63])=[O:62])[CH2:58][O:59][C@@H:10]2[CH2:9][C@@H:8]1[OH:64])=[O:6].[C:41]1(=[O:42])[O:47][C:45](=[O:46])[CH2:44][CH2:43]1.[CH3:1][C:2]1[C@@H:19]([O:20][C:21]([C@H:23]([OH:40])[C@@H:24]([NH:31][C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:33])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:22])[CH2:18][C@:14]2([OH:48])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([O:66][C:67]([CH3:69])=[O:68])[C:5]([C@@:7]1([CH3:65])[C@H:12]([C@@H:13]2[O:49][C:50]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[O:51])[C@:11]2([O:60][C:61]([CH3:63])=[O:62])[CH2:58][O:59][C@@H:10]2[CH2:9][C@@H:8]1[OH:64])=[O:6]