Paclitaxel → Fmoc-Leu PABC Paclitaxel

HRID 237415

反応式

HRID 237415 の反応式
[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]

参加物

5

反応物 2

HCID 36314PaclitaxelHCID 131731174Fmoc-Leu PABC

生成物 1

HCID 131731173Fmoc-Leu PABC Paclitaxel収率 93%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-baa64055c72c46edb4b6fb547eebad34
出典データセット
uspto-grants-2014_02
特許番号
US08642555B2

関連ノート

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