Triethylamine → Methyl trans-2-{[(cyanomethyl)amino]carbonyl}cyclopentanecarboxylate
反応式
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10]([OH:12])=O)=[O:4].Cl.[NH2:14][CH2:15][C:16]#[N:17].F[P-](F)(F)(F)(F)F.N1([PH+](N2CCCC2)N2CCCC2)CCCC1.C(N(CC)CC)C>CN(C)C=O>[C:15]([CH2:16][NH:17][C:10]([C@@H:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[C:3]([O:2][CH3:1])=[O:4])=[O:12])#[N:14]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 0 °C
実験手順
Cyclopentane-1,2-dicarboxylic acid monomethyl ester (2.21 g, 12.8 mmol), 2-aminoacetonitrile hydrochloride (1.48 g, 16.0 mmol) and benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP) (7.34 g, 14.1 mmol) were dissolved in dimethylformamide (26 mL) and the reaction mixture was cooled to 0° C. Triethylamine (4.9 mL, 35 mmol) was added and the reaction mixture was stirred at ambient temperature for 3 h. The reaction mixture was partitioned between water (150 mL) and ethyl acetate (100 mL). The product was extracted into ethyl acetate, washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on silica gel with 3:2 ethyl acetate:hexanes eluent to give methyl trans-2-{[(cyanomethyl)amino]carbonyl}cyclopentanecarboxylate as a colorless solid.
後処理
- customThe reaction mixture was partitioned between water (150 mL) and ethyl acetate (100 mL)
- extractionThe product was extracted into ethyl acetate
- washwashed with saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe residue was chromatographed on silica gel with 3:2 ethyl acetate
出典と根拠
- ORDレコード
- ord-00527ddaf1df475ca700b359b698bed5
- 出典データセット
- uspto-grants-2008_05
- 特許番号
- US07371747B2
反応ノート
読み込み中…