Reaktion #2146713

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 61.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeOn 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
   SonstigeThe organic layer was separated
6. 6
   Waschenwashed with saturated aqueous NaHCO3 solution (20 mL), water (2×20 mL), and brine (2×20 mL)
7. 7
   TrocknenThe solution was dried (Na2SO4)
8. 8
   Einengenconcentrated under vacuum
9. 9
   SonstigeThe residue was purified by chromatography (CH2Cl2/MeOH 9:1)

Vorschrift

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.

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