Daunorubicin → N-(Cyanomethyl)daunorubicin

HRID 280904ノート

反応式

HRID 280904 の反応式
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]

参加物

5

反応物 3

HCID 30323DaunorubicinHCID 69356IodoacetonitrileHCID 517045Sodium Acetate

生成物 1

HCID 113614N-(Cyanomethyl)daunorubicin

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  1. customthe dark red mixture thus obtained

出典と根拠

ORDレコード
ord-6c6054c288f24fa99da08e7fb5584de2
出典データセット
uspto-grants-1986_05
特許番号
US04591637

反応ノート

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