Taurine → Succinic anhydride

HRID 345972

Reaktionsgleichung

Reaktionsgleichung von HRID 345972
[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]

Komponenten

6

Edukt 2

HCID 1123TaurineHCID 25024567Paclitaxel Succinate

Produkt 3

HCID 7922Succinic anhydrideHCID 36314PaclitaxelHCID 25024567Paclitaxel Succinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customin high yield

Quellen und Nachweise

ORD-Eintrag
ord-f1b9b1b1b7414784b308a6e5af160e9b
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05059699

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