Реакция #53250

Уравнение реакции

cholesterol ethylenediamine 2,2′-dipyridyldisulfide

2-iminothiolane

2,2′-dipyridyl disulfide

cholesterol ethylenediamine

diisopropylethylamine

cholesterol ethylenediamine

→

Cholesterol ethylamidinopropyl-pyridyldisulfide

Растворители

methanol

methanol

DCM

Условия реакции

Обработка

1. 1
   Другоеorganic solvent was roto-evaporated away
2. 2
   workup.ADDITIONApproximately 800 mL of acetonitrile was added
3. 3
   Другоеto precipitate the crude product
4. 4
   ФильтрацияThe solid was then collected by filtration onto a Whatman #5
5. 5
   Фильтрацияfilter apparatus
6. 6
   Промывкаrinsed several times with acetonitrile
7. 7
   Другоеair-dried
8. 8
   workup.DISSOLUTIONThe crude solid was dissolved in a minimal volume of chloroform
9. 9
   Другоеchromatographically purified

Методика

Pure cholesterol-ethylenediamine (10 mmol) was dissolved in 300 mL of DCM. 100 mmol of 2,2′-dipyridyl disulfide was dissolved in 100 mL of methanol and added to the cholesterol-ethylenediamine solution plus 20 mmol of diisopropylethylamine. 15 mmol of 2-iminothiolane was dissolved in 50 mL of methanol and then drop-wise added to the cholesterol-ethylenediamine/2,2′-dipyridyldisulfide solution over 30 minutes at R.T. Following an overnight R.T. stir, organic solvent was roto-evaporated away using medium vacuum until a minimal sample volume remained. Approximately 800 mL of acetonitrile was added to precipitate the crude product. The solid was then collected by filtration onto a Whatman #5 filter apparatus, rinsed several times with acetonitrile and then air-dried. The crude solid was dissolved in a minimal volume of chloroform and chromatographically purified using a silica column. The purified product presented a single TLC spot (4:1 chloroform/methanol), and a single peak (parent ion M+H=685) was identified by positive mode electrospray.

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