Paclitaxel → Fmoc-Leu PABC Paclitaxel

HRID 237415

반응식

HRID 237415 반응식
[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]

참가 물질

5

반응물 2

HCID 36314PaclitaxelHCID 131731174Fmoc-Leu PABC

생성물 1

HCID 131731173Fmoc-Leu PABC Paclitaxel수율 93%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-baa64055c72c46edb4b6fb547eebad34
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642555B2

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