Daunorubicin → N-(Cyanomethyl)daunorubicin

HRID 280904노트

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HRID 280904 반응식
C([O-])(=O)C.[Na+].I[CH2:7][C:8]#[N:9].[CH3:10][C@@H:11]1[O:16][C@@H:15]([O:17][C@@H:18]2[C:23]3=[C:24]([OH:41])[C:25]4[C:37](=[O:38])[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][C:35]=5[O:39][CH3:40])[C:29](=[O:30])[C:26]=4[C:27]([OH:28])=[C:22]3[CH2:21][C@@:20]([OH:45])([C:42]([CH3:44])=[O:43])[CH2:19]2)[CH2:14][C@H:13]([NH2:46])[C@@H:12]1[OH:47]>CN(C=O)C>[CH3:10][CH:11]1[O:16][CH:15]([O:17][CH:18]2[C:23]3[C:22](=[C:27]([OH:28])[C:26]4[C:29](=[O:30])[C:31]5[CH:32]=[CH:33][CH:34]=[C:35]([O:39][CH3:40])[C:36]=5[C:37](=[O:38])[C:25]=4[C:24]=3[OH:41])[CH2:21][C:20]([OH:45])([C:42]([CH3:44])=[O:43])[CH2:19]2)[CH2:14][CH:13]([NH:46][CH2:7][C:8]#[N:9])[CH:12]1[OH:47]

참가 물질

5

반응물 3

HCID 30323DaunorubicinHCID 69356IodoacetonitrileHCID 517045Sodium Acetate

생성물 1

HCID 113614N-(Cyanomethyl)daunorubicin

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A sample of 0.017 grams (0.21 mmol) of anhydrous sodium acetate and 15 μl (0.033 g, 0.197 mmol) of iodoacetonitrile were added to a solution of 0.065 grams (0.123 mmol) of daunorubicin, free base, in 1 ml of dry DMF, and the dark red mixture thus obtained stirred at room temperature in the dark for 44 hours until thin layer chromatography (TLC) run on aliquots of the reaction mixture showed conversion to the desired product. The reaction mixture was then evaporated at low temperature and pressure (about 35°, <5 mm), the residue dissolved in 10 ml chloroform/methanol (9/1) and the solution washed with acetic acid, water, and sodium bicarbonate and dried. The organic layer was evaporated, and the residue further purified to obtain 0.059 g (84%) of the desired N-cyanomethylDau. Daunorubicin (0.010 g) was recovered from the acetic acid extract.

후처리

  1. customthe dark red mixture thus obtained

출처 및 근거

ORD 기록
ord-6c6054c288f24fa99da08e7fb5584de2
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04591637

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