반응 #737271

반응 방정식

Monensin sodium salt

diazabicyclo [2.2.2] octane

benzyl bromide

benzyl bromide

→

Monensin Benzyl Ester

용매

acetonitrile

반응 조건

후처리

1. 1
   기타The solvent was evaporated
2. 2
   workup.DISSOLUTIONthe crude product redissolved in dichloromethane
3. 3
   세척washed with deionized water
4. 4
   건조dried over magnesium sulfate
5. 5
   기타The crude product was chromatographed on silica gel eluting with hexane-ethyl acetate gradient
6. 6
   세척Excess benzyl bromide eluted from the column
7. 7
   기타was isolated as a colorless oil
8. 8
   기타after removal of the solvent (280 mg, 26%), (MS, positive ion ESI showed 783 peak; calc. for sodiated product 783)

실험 절차

Monensin sodium salt (1.0 g, 1.4 mmol) in acetonitrile (20 ml) was treated with diazabicyclo [2.2.2] octane (0.3 g, 2.7 mmol) followed by benzyl bromide (2 g, 11.7 mmol) and cryptand [2.2.2]. The reaction mixture was stirred at room temperature with exclusion of light for 14 days. After 10 days an additional quantity of benzyl bromide (2 g, 11.7 mmol) was added. The solvent was evaporated and the crude product redissolved in dichloromethane, washed with deionized water and dried over magnesium sulfate. The crude product was chromatographed on silica gel eluting with hexane-ethyl acetate gradient. Excess benzyl bromide eluted from the column first followed by benzylmonensin which was isolated as a colorless oil after removal of the solvent (280 mg, 26%), (MS, positive ion ESI showed 783 peak; calc. for sodiated product 783). This compound has been reported previously (Tsukube J. Org. Chem. 56, 875, 1991).

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