反応式
[CH3:1][C@@H:2]([C:9]([OH:11])=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[NH2:39][C@@H:40]1[CH2:49][C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH2:42][C@H:41]1[OH:50].CN1CCOCC1>C(Cl)Cl.C(OCC)(=O)C>[C:3]1([C@@H:2]([CH3:1])[C:9]([NH:39][C@@H:40]2[CH2:49][C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[CH2:42][C@H:41]2[OH:50])=[O:11])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1参加物
反応条件
- 温度
- 0 °C
実験手順
Under argon to a solution of R-(-)-2-phenylpropionic acid (505 mg) in methylene chloride (10 ml) at 0° C. was added hydroxybenzotriazole, hydrate (530 mg) and dicyclohexylcarbodiimide (718 mg). The mixture was stirred at 0° C. for 10 minutes before addition of racemic trans-3-amino-1,2,3,4-tetrahydro-2-naphthalenol, hydrochloride (723 mg) and N-methylmorpholin (438 mg) in methylene chloride (5 ml). Stirring was maintained at 0° C. for 3 hours and at room temperature overnight. The reaction mixture was diluted with ethyl acetate and filtered. Evaporation of solvent gave the crude mixture of diastereoisomer A and diastereoisomer B. The diastereoisomer separation was achieved by chromatography on silica gel [160 g, elution with ethyl acetate: cyclohexane, 1:9 (700 ml), 2:8 (1 1), 3:7 (1 1) 2:3 (1 1) and 1:1 (1 1)]. Diastereoisomer A obtained as a white solid (232 mg) was recrystallized in ethyl acetate/cyclohexane, m.p. 158° C., Rf=0.30 (silica gel, ethyl acetate:cyclohexane, 1:1). Diastereoisomer B was recovered as a white solid (250 mg) and recrystallized in ethyl acetate, m.p. 179-180° C., Rf=0.40 (silica gel, ethyl acetate:cyclohexane, 1:1).
後処理
- filtrationfiltered
- customEvaporation of solvent
- customgave the crude
- additionmixture of diastereoisomer A and diastereoisomer B
- customThe diastereoisomer separation
出典と根拠
- ORDレコード
- ord-defe3c8f2f19491792e952fa711b1861
- 出典データセット
- uspto-grants-1992_04
- 特許番号
- US05106861
関連ノート
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