Benzyl Bromide → Benzyl betulinate

HRID 241546

Reaktionsgleichung

Reaktionsgleichung von HRID 241546
[CH3:1][C:2]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([C:31]([OH:33])=[O:32])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:30])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C@@H:16]([OH:29])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[CH2:40](Br)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C1(C)C=CC=CC=1.C(OCC)C>CN(C)C=O.O>[CH3:3][C:2]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([C:31]([O:33][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:32])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:30])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:27])([CH3:28])[C@@H:16]([OH:29])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:1]

Komponenten

7

Edukt 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 64971Betulinic AcidHCID 22238780Ether toluene

Produkt 1

HCID 44626706Benzyl betulinateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a mixture of betulinic acid (2) (500 mg; 1.1 mmol) and potassium carbonate (276 mg; 2.0 mmol) in N,N-dimethylformamide, hereinafter DMF (20 ml), benzylbromide (178 μl; 1.5 mmol) was added and the reaction mixture was stirred at room temperature for 24 h. The course of the reaction was monitored by TLC (toluene/diethyl ether 10:1). The reaction mixture was then diluted with ten-fold excess of water and extracted into ethyl acetate. Combined organic phases were shaken three times with 5% HCl, three times with water, dried with magnesium sulphate and the solvents were evaporated at a rotary vacuum evaporator. The evaporate was purified by column chromatography on silica gel, toluene being the mobile phase. The obtained crude benzyl betulinate (517 mg; 86%) was used without purification in the next step.

Aufarbeitung

  1. extractionextracted into ethyl acetate
  2. stirringCombined organic phases were shaken three times with 5% HCl, three times with water
  3. dry with materialdried with magnesium sulphate
  4. customthe solvents were evaporated at a rotary vacuum evaporator
  5. customThe evaporate was purified by column chromatography on silica gel, toluene being the mobile phase

Quellen und Nachweise

ORD-Eintrag
ord-80e08db3965248e4821bbf7ceeb21451
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653056B2

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