1,8-Diazabicyclo(5.4.0)undec-7-ene → H-Leu PABC Paclitaxel

HRID 237416Notes

Reaction equation

HRID 237416 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:27][C:28]([NH:39][CH2:40][CH:41]([OH:57])[CH2:42][O:43][C:44]1[C:49]2[C:50]3[C:55]([NH:56][C:48]=2[CH:47]=[CH:46][CH:45]=1)=[CH:54][CH:53]=[CH:52][CH:51]=3)([C:30]1[CH:35]=[CH:34][C:33]([N:36]=[N+:37]=[N-:38])=[CH:32][CH:31]=1)[CH3:29].[CH3:58][C:59]1[C@@H:76]([O:77][C:78]([C@H:80]([OH:97])[C@@H:81]([NH:88][C:89]([C:91]2[CH:92]=[CH:93][CH:94]=[CH:95][CH:96]=2)=[O:90])[C:82]2[CH:83]=[CH:84][CH:85]=[CH:86][CH:87]=2)=[O:79])[CH2:75][C@:71]2([OH:98])[C:72]([CH3:74])([CH3:73])[C:60]=1[C@@H:61]([O:116][C:117]([CH3:119])=[O:118])[C:62]([C@@:64]1([CH3:115])[C@H:69]([C@@H:70]2[O:99][C:100]([C:102]2[CH:103]=[CH:104][CH:105]=[CH:106][CH:107]=2)=[O:101])[C@:68]2([O:110][C:111]([CH3:113])=[O:112])[CH2:108][O:109][C@@H:67]2[CH2:66][C@@H:65]1[OH:114])=[O:63].N12CCCN=C1CCCCC2>O1CCCC1>[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:29][C:28]([NH:39][CH2:40][CH:41]([OH:57])[CH2:42][O:43][C:44]1[C:49]2[C:50]3[C:55]([NH:56][C:48]=2[CH:47]=[CH:46][CH:45]=1)=[CH:54][CH:53]=[CH:52][CH:51]=3)([C:30]1[CH:35]=[CH:34][C:33]([N:36]=[N+:37]=[N-:38])=[CH:32][CH:31]=1)[CH3:27].[CH3:58][C:59]1[C@@H:76]([O:77][C:78]([C@H:80]([OH:97])[C@@H:81]([NH:88][C:89]([C:91]2[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=2)=[O:90])[C:82]2[CH:83]=[CH:84][CH:85]=[CH:86][CH:87]=2)=[O:79])[CH2:75][C@:71]2([OH:98])[C:72]([CH3:73])([CH3:74])[C:60]=1[C@@H:61]([O:116][C:117]([CH3:119])=[O:118])[C:62]([C@@:64]1([CH3:115])[C@H:69]([C@@H:70]2[O:99][C:100]([C:102]2[CH:107]=[CH:106][CH:105]=[CH:104][CH:103]=2)=[O:101])[C@:68]2([O:110][C:111]([CH3:113])=[O:112])[CH2:108][O:109][C@@H:67]2[CH2:66][C@@H:65]1[OH:114])=[O:63]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 131731173Fmoc-Leu PABC Paclitaxel

Product 1

HCID 131731175H-Leu PABC PaclitaxelYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8 (0.50 g, 0.37 mmol) was treated with 1% of 1,8-Diazabicyclo[5.4.0]undec-7-en (DBU) in Tetrahydrofuran (THF) (10 mL) for 45 seconds at room temperature and the product was precipitated by 1 M HCl in diethyl ether (500 mL). Then it was purified on a silica gel column using chloroform/methanol (7:1) to afford 9 (350 mg, 84%) as a white powder. ESI-MS (5 kV, MeOH): m/z (%)=1116.1 (100) [M+H]+; HPLC (230 nm): >95%.

Workup

  1. customthe product was precipitated by 1 M HCl in diethyl ether (500 mL)
  2. customThen it was purified on a silica gel column

Sources & evidence

ORD record
ord-8c1d3a206c64464f833a20ec8b9f0da5
Source dataset
uspto-grants-2014_02
Patent number
US08642555B2

Reaction notes

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