반응 #1929091

반응 방정식

bromoacetylbromide

aminobenzyl bisphosphonate

Tetraallyl 1-(4-aminobenzyl)methylenebisphosphonate

pyridine

→

bromide

수율 76.0%

Tetraallyl 1-(4-bromoacetamidobenzyl)methylenebisphosphonate

수율 76.0%

용매

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   세척washed with aqueous 1N HCl solution, saturated NaHCO3 solution, and saturated NaCl solution
2. 2
   건조dried over MgSO4
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   기타The crude product was purified by flash chromatography on silica gel using a gradient of 0-10% MeOH in CH2Cl2 as eluant

실험 절차

To a solution of aminobenzyl bisphosphonate 27 (180 mg, 0.41 mmol) in CH2Cl2 (5 mL) at 0° C. was added pyridine (49 μL, 0.61 mmol) followed by bromoacetylbromide (35 μL, 0.41 mmol). The reaction mixture was stirred at 0° C. for 30 min and at room temperature for another 2.5 h. The reaction mixture was diluted with CH2Cl2, washed with aqueous 1N HCl solution, saturated NaHCO3 solution, and saturated NaCl solution, then dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel using a gradient of 0-10% MeOH in CH2Cl2 as eluant to provide bromide 28 as a clear yellow oil (175 mg, 3.11×10−4 mol, 76%). 1H NMR (400 MHz, CDCl3) δ 2.72 (tt, J=23.9, 6.2 Hz, 1H), 3.26 (dt, J=16.3, 6.1 Hz, 2H), 4.02 (s, 2H), 4.48-4.62 (m, 8H), 5.20-5.24 (m, 4H), 5.29-5.35 (m, 4H), 5.83-5.94 (m, 4H), 7.25-7.28 (m, 2H), 7.42-7.46 (m, 2H), 8.11 (bs, 1H).

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