Taurine → Succinic anhydride

HRID 345972

반응식

HRID 345972 반응식
[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]

참가 물질

6

반응물 2

HCID 1123TaurineHCID 25024567Paclitaxel Succinate

생성물 3

HCID 7922Succinic anhydrideHCID 36314PaclitaxelHCID 25024567Paclitaxel Succinate

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  1. customin high yield

출처 및 근거

ORD 기록
ord-f1b9b1b1b7414784b308a6e5af160e9b
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05059699

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