Trifluoroacetic acid → (1S,2R,3S,5R)-3-Amino-5-(6-amino-2-chloro-purin-9-yl)-cyclopentane-1,2-diol trifluoroacetate
反応式
COC1C=CC(C([NH:18][C:19]2[N:27]=[C:26]([Cl:28])[N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][N:23]3[C@@H:29]2[CH2:33][C@H:32]([N:34](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C@@H:31]([OH:49])[C@H:30]2[OH:50])C2C=CC(OC)=CC=2)=CC=1.[C:51]([OH:57])([C:53]([F:56])([F:55])[F:54])=[O:52]>ClCCl>[F:54][C:53]([F:56])([F:55])[C:51]([OH:57])=[O:52].[NH2:34][C@H:32]1[CH2:33][C@@H:29]([N:23]2[CH:22]=[N:21][C:20]3[C:24]2=[N:25][C:26]([Cl:28])=[N:27][C:19]=3[NH2:18])[C@H:30]([OH:50])[C@@H:31]1[OH:49]参加物
4
反応物 2
生成物 1
試薬・触媒・溶媒 1
実験手順
(1R,2S,3R,5S)-3-(6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-2-chloro-purin-9-yl)-5-(di-Boc-amino)-cyclopentane-1,2-diol (600 mg, 0.84 mmol) is dissolved in dichloromethane (4 ml). TFA (2 ml) is added and the reaction mixture is stirred at room temperature. The reaction is shown to be complete by LCMS after 18 hours. The solvent is removed in vacuo and the title compound is obtained after purification by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water −0.1% TFA). 1H nmr (MeOD, 400 MHz); 8.10 (s, 1H), 4.80 (m, 1H), 4.60 (m, 1H), 4.30 (m, 1H), 3.60 (m, 1H), 2.85 (m, 1H), 2.30 (m, 1H). MS (ES+) m/e 285 (MH+).