Ethylenediamine → Cholesterol Ethylenediamine

HRID 843499

Reaktionsgleichung

Reaktionsgleichung von HRID 843499
ClC([O:4][C@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:31])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:6]1)=O.[CH2:32]([NH2:35])[CH2:33][NH2:34].C(N(C(C)C)CC)(C)C>ClCCl>[CH3:21][CH:19]([CH2:18][CH2:17][CH2:16][C@H:15]([C@@H:14]1[C@:23]2([CH3:31])[C@H:11]([C@H:10]3[C@H:26]([CH2:25][CH2:24]2)[C@:27]2([CH3:30])[C:7]([CH2:6][C@H:5]([CH2:29][CH2:28]2)[OH:4])=[CH:8][CH2:9]3)[CH2:12][CH2:13]1)[CH3:22])[CH3:20].[CH2:32]([NH2:35])[CH2:33][NH2:34]

Komponenten

5

Edukt 3

HCID 3301Ethylenediamine2×HCID 81531DiisopropylethylamineHCID 111262Cholest-5-en-3-ol (3beta)-, 3-(carbonochloridate)2×

Produkt 1

HCID 69752158Cholesterol Ethylenediamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Solid cholesterol chloroformate (10 mmol) was dissolved in 100 mL of dichloromethane (DCM). In a separate flask 0.5 mol ethylenediamine was diluted with 200 mL of DCM and 20 mmol diisopropylethylamine. While stirring, the cholesterol chloroformate solution was drop-wise added to the ethylenediamine solution over a 30 minute period at room temperature (R.T.). Following an overnight R.T. stir, organic solvent was roto-evaporated away using medium vacuum until a minimal sample volume remained. Approximately 400 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=474) was identified by positive mode electrospray.

Aufarbeitung

  1. stirringstir
  2. customorganic solvent was roto-evaporated away
  3. additionApproximately 400 mL of acetonitrile was added
  4. customto precipitate the crude product
  5. filtrationThe solid was then collected by filtration onto a Whatman #5
  6. filtrationfilter apparatus
  7. washrinsed several times with acetonitrile
  8. customair-dried
  9. dissolutionThe crude solid was dissolved in a minimal volume of chloroform
  10. customchromatographically purified

Quellen und Nachweise

ORD-Eintrag
ord-a69e9a649c4e4f05b277a2012352596f
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06379698B1

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