Taurine → Succinic anhydride

HRID 345972

Reaction equation

HRID 345972 reaction equation
[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]

Participants

6

Reactant 2

HCID 1123TaurineHCID 25024567Paclitaxel Succinate

Product 3

HCID 7922Succinic anhydrideHCID 36314PaclitaxelHCID 25024567Paclitaxel Succinate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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

  1. customin high yield

Sources & evidence

ORD record
ord-f1b9b1b1b7414784b308a6e5af160e9b
Source dataset
uspto-grants-1991_10
Patent number
US05059699

Linked notes

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