Methyl (2S)-2-amino-5-(5-{[(2-fluorophenyl)methyl]oxy}-2-pyridinyl)-4-pentynoate → Methyl (2S)-5-(5-{[(2-fluorophenyl)methyl]oxy}-2-pyridinyl)-3,4-dihydro-2H-pyrrole-2-carboxylate
反応式
[NH2:1][C@@H:2]([CH2:7][C:8]#[C:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[CH:12][N:11]=1)[C:3]([O:5][CH3:6])=[O:4]>C(#N)C.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]2[CH2:8][CH2:7][C@@H:2]([C:3]([O:5][CH3:6])=[O:4])[N:1]=2)=[N:11][CH:12]=1参加物
4
反応物 1
生成物 1
試薬・触媒・溶媒 2
実験手順
To a solution of methyl (2S)-2-amino-5-(5-{[(2-fluorophenyl)methyl]oxy}-2-pyridinyl)-4-pentynoate (D84, 300 mg, 0.91 mmol) in acetonitrile was added silver triflate (24 mg, 0.091 mmol) and the mixture was stirred for 60 hours at room temperature. The solvent was evaporated and the residue diluted with water and extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered and evaporated affording the title compound as a yellow solid (300 mg, quantitative). Rt (HPLC): 3.58 min; MS: (ES/+) m/z: 329 [MH]+ C18H17FN2O3 requires 328.