Paclitaxel → Paclitaxel cephalomannine

HRID 1109266

Reaction equation

HRID 1109266 reaction equation
[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: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:41])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([O:59][C:60]([CH3:62])=[O:61])[C:5]([C@@:7]1([CH3:58])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][C@@H:8]1[OH:57])=[O:6].[CH3:63]/[CH:64]=[C:65](/[C:67]([NH:69][C@H:70]([C@@H:77]([OH:122])[C:78]([O:80][C@@H:81]1[C:102]([CH3:103])=[C:101]2[C:104]([CH3:106])([CH3:105])[C@:83]([OH:121])([C@@H:84]([O:112][C:113]([C:115]3[CH:116]=[CH:117][CH:118]=[CH:119][CH:120]=3)=[O:114])[C@@H:85]3[C@:90]4([O:93][C:94]([CH3:96])=[O:95])[CH2:91][O:92][C@@H:89]4[CH2:88][C@H:87]([OH:97])[C@@:86]3([CH3:111])[C:98]([C@@H:100]2[O:107][C:108]([CH3:110])=[O:109])=[O:99])[CH2:82]1)=[O:79])[C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)=[O:68])\[CH3:66]>C(OCC)(=O)C.O=[Pt]=O>[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:41])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([O:59][C:60]([CH3:62])=[O:61])[C:5]([C@@:7]1([CH3:58])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][C@@H:8]1[OH:57])=[O:6].[CH3:63]/[CH:64]=[C:65](/[C:67]([NH:69][C@H:70]([C@@H:77]([OH:122])[C:78]([O:80][C@@H:81]1[C:102]([CH3:103])=[C:101]2[C:104]([CH3:105])([CH3:106])[C@:83]([OH:121])([C@@H:84]([O:112][C:113]([C:115]3[CH:116]=[CH:117][CH:118]=[CH:119][CH:120]=3)=[O:114])[C@@H:85]3[C@:90]4([O:93][C:94]([CH3:96])=[O:95])[CH2:91][O:92][C@@H:89]4[CH2:88][C@H:87]([OH:97])[C@@:86]3([CH3:111])[C:98]([C@@H:100]2[O:107][C:108]([CH3:110])=[O:109])=[O:99])[CH2:82]1)=[O:79])[C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)=[O:68])\[CH3:66]

Participants

5

Reactant 2

HCID 36314PaclitaxelHCID 6436208Cephalomannine

Product 1

HCID 86586153Paclitaxel cephalomannine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 262 mg quantity of an approximately 50/50 mixture of taxol and cephalomannine was dissolved in 10 mL of ethyl acetate in a 100 mL round bottom flask with magnetic stirring. Then 20 mg of PtO2 was added and the flask was attached to a hydrogenation apparatus. After flushing the flask five times with hydrogen gas, the solution was stirred at room temperature. After 1 hour, the flask was removed from the hydrogenation apparatus and the solution filtered through Celite to remove the catalyst. The resulting solution was evaporated to dryness under vacuum. The result was 262 mg (100%) of a mixture of taxol and dihydrocephalomannine. No further purification was performed and the sample was used as is in the next step.

Workup

  1. customAfter flushing the flask five times with hydrogen gas
  2. customthe flask was removed from the hydrogenation apparatus
  3. filtrationthe solution filtered through Celite
  4. customto remove the catalyst
  5. customThe resulting solution was evaporated to dryness under vacuum
  6. customNo further purification

Sources & evidence

ORD record
ord-a54f79637bfe4f938d92d89b1bc13c39
Source dataset
uspto-grants-1994_06
Patent number
US05319112

Linked notes

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