Paclitaxel → Fmoc-Leu PABC Paclitaxel

HRID 237415

Reaktionsgleichung

Reaktionsgleichung von HRID 237415
[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].[NH:63]([C:72]([O:74][CH2:75][CH:76]1[C:88]2[C:83](=[CH:84][CH:85]=[CH:86][CH:87]=2)[C:82]2[C:77]1=[CH:78][CH:79]=[CH:80][CH:81]=2)=[O:73])[C@H:64]([C:69]([OH:71])=[O:70])[CH2:65][CH:66]([CH3:68])[CH3:67].[CH3:89][C:90]([NH:101][CH2:102][CH:103]([OH:119])[CH2:104][O:105][C:106]1[C:111]2[C:112]3[C:117]([NH:118][C:110]=2[CH:109]=[CH:108][CH:107]=1)=[CH:116][CH:115]=[CH:114][CH:113]=3)([C:92]1[CH:97]=[CH:96][C:95]([N:98]=[N+:99]=[N-:100])=[CH:94][CH:93]=1)[CH3:91]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[NH:63]([C:72]([O:74][CH2:75][CH:76]1[C:77]2[C:82](=[CH:81][CH:80]=[CH:79][CH:78]=2)[C:83]2[C:88]1=[CH:87][CH:86]=[CH:85][CH:84]=2)=[O:73])[C@H:64]([C:69]([OH:71])=[O:70])[CH2:65][CH:66]([CH3:68])[CH3:67].[CH3:91][C:90]([NH:101][CH2:102][CH:103]([OH:119])[CH2:104][O:105][C:106]1[C:111]2[C:112]3[C:117]([NH:118][C:110]=2[CH:109]=[CH:108][CH:107]=1)=[CH:116][CH:115]=[CH:114][CH:113]=3)([C:92]1[CH:97]=[CH:96][C:95]([N:98]=[N+:99]=[N-:100])=[CH:94][CH:93]=1)[CH3:89].[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]

Komponenten

5

Edukt 2

HCID 36314PaclitaxelHCID 131731174Fmoc-Leu PABC

Produkt 1

HCID 131731173Fmoc-Leu PABC PaclitaxelAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Paclitaxel (0.37 g, 0.44 mmol) and 4-Dimethylaminopyridine (DMAP) (0.05 g, 0.44 mmol) were added to a solution of 7 (0.27 g, 0.44 mmol) in anhydrous DCM (15 mL), and the reaction was stirred in the dark at room temperature for 24 hours. Subsequently, DCM (20 mL) was added and the reaction mixture was extracted with NaHCO3, brine and dried over sodium sulphate. The residue was purified on a silica gel column using ethyl acetate/hexane (1:1) to afford 8 (550 mg, 93%) as a white powder. ESI-MS (5 kV, MeOH): m/z (%)=1360.1 (100) [M+Na]+; HPLC (230 nm): >95%.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with NaHCO3, brine
  2. dry with materialdried over sodium sulphate
  3. customThe residue was purified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-baa64055c72c46edb4b6fb547eebad34
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642555B2

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