تفاعل #2146713

معادلة التفاعل

21

5-tert-Butoxycarbonylamino-5-{2-[4-(5-(4-(4-(4,4-difluoro-1,3,5,7-tetramethyl-3a,4a-diaza-s-indacen-8-yl)phenyl)-1,2,3-triazol-1-yl)pentyl)phenyl]ethyl}-2,2-dimethyl-1,3-dioxane

BF3.OEt2

→

3

المردود 61.0%

2-Amino-2-{2-[4-(5-(4-(4-(4,4-difluoro-1,3,5,7-tetramethyl-3a,4a-diaza-s-indacen-8-yl)phenyl)-1,2,3-triazol-1-yl)pentyl)phenyl]ethyl}propane-1,3-diol

المردود 61.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىOn the disappearance of 21 (˜5 h), the reaction was quenched
2. 2
   workup.ADDITIONby adding saturated aqueous NaHCO3 solution (10 mL)
3. 3
   workup.STIRRINGAfter the mixture was stirred for 30 min
4. 4
   workup.ADDITIONCH2Cl2 (30 mL) was added
5. 5
   أخرىThe organic layer was separated
6. 6
   غسيلwashed with saturated aqueous NaHCO3 solution (20 mL), water (2×20 mL), and brine (2×20 mL)
7. 7
   تجفيفThe solution was dried (Na2SO4)
8. 8
   تركيزconcentrated under vacuum
9. 9
   أخرىThe residue was purified by chromatography (CH2Cl2/MeOH 9:1)

الإجراء التجريبي

To a cold solution (0° C.) of 21 (40 mg, 50.3 μmol) in dry CH2Cl2 (10 mL) were added 4 Å molecular sieves (0.40 g) and BF3.OEt2 (0.18 g, 1.27 mmol) with vigorous stirring. The mixture was stirred at 0° C., and the reaction was monitored by TLC (hexanes/EtOAc 2:1). On the disappearance of 21 (˜5 h), the reaction was quenched by adding saturated aqueous NaHCO3 solution (10 mL). After the mixture was stirred for 30 min, CH2Cl2 (30 mL) was added. The organic layer was separated and washed with saturated aqueous NaHCO3 solution (20 mL), water (2×20 mL), and brine (2×20 mL). The solution was dried (Na2SO4) and concentrated under vacuum. The residue was purified by chromatography (CH2Cl2/MeOH 9:1) to give 3 (20.1 mg, 61%). 1HNMR δ 7.96 (d, 2H, J=8.4 Hz), 7.84 (s, 1H), 7.34 (d, 2H, J=8.4 Hz), 7.11-7.01 (m, 4H), 5.98 (s, 2H), 4.39 (t, 2H, J=7.2 Hz), 3.85-3.57 (m, 4H), 3.56-3.01 (br s, 4H), 2.61-2.51 (m, 4H), 2.55 (s, 6H), 2.00-1.92 (m, 2H), 1.70-1.56 (m, 2H), 1.43 (s, 6H), 1.46-1.05 (m, 4H); 13C NMR δ 155.6, 147.0, 143.0, 141.2, 139.8, 138.6, 134.7, 131.4, 128.6, 128.5, 128.3, 126.3, 122.5, 121.3, 119.9, 50.4, 35.1, 30.8, 30.3, 29.7, 29.4, 26.0, 14.6, 14.1; 19F NMR δ-146.1 (m). HRMS m/z: calcd for C37H46BF2N6O2 (MH+), 655.3737; found, 655.3746.

المصدر