1,1-Dichloroethane → HCID 90409693, 화합물

반응식

[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C:9]1[C:14]([F:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19](Cl)=[C:18]([F:23])[CH:17]=2)[N:12]=[C:11]([C:24]([O:26][CH3:27])=[O:25])[C:10]=1[Cl:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.[Cl:43]C(Cl)C>>[C:1]([O:5][C:6]([NH:8][C:9]1[C:14]([F:15])=[C:13]([C:16]2([Cl:43])[CH:21]=[CH:20][CH:19]=[C:18]([F:23])[CH2:17]2)[N:12]=[C:11]([C:24]([O:26][CH3:27])=[O:25])[C:10]=1[Cl:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

반응물 3

HCID 63651,1-Dichloroethane

HCID 6422Trifluoroacetic acid

HCID 90409505HCID 90409505, 화합물

생성물 1

HCID 90409693HCID 90409693, 화합물수율 98%

실험 절차

Methyl 4-(bis(tert-butoxycarbonyl)amino)-3-chloro-6-(4-chloro-3-fluorophenyl)-5-fluoropicolinate (2.1 g, 3.94 mmol) was dissolved in dichloroethane (20 mL) and trifluoroacetic acid (0.598 mL, 7.76 mmol) was added at rt. The reaction mixture was stirred overnight at room temperature then concentrated under vacuum. The product was purified by flash chromatography (SiO2, eluting with 2-20% ethyl acetate in dichloromethane) to provide the title compound as a white solid (1.64 g, 98%): 1H NMR (300 MHz, CDCl3) δ 7.80 (dd, J=22.0, 8.5 Hz, 2H), 7.50 (dd, J=8.3, 7.6 Hz, 1H), 6.51 (s, 1H), 4.02 (s, 3H), 1.56 (s, 9H); ESIMS m/z 431 ([M−H]−).