Benzyl Bromide → Benzyl betulinate

HRID 2405468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2405468
[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>CN(C=O)C>[OH:29][C@H:16]1[CH2:15][CH2:14][C@@:13]2([CH3:30])[C@@H:18]([CH2:19][CH2:20][C@:21]3([CH3:26])[C@@H:12]2[CH2:11][CH2:10][C@H:9]2[C@@:22]3([CH3:25])[CH2:23][CH2:24][C@@:7]3([C:31]([O:33][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[O:32])[CH2:6][CH2:5][C@@H:4]([C:2]([CH3:1])=[CH2:3])[C@@H:8]32)[C:17]1([CH3:27])[CH3:28]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 64971Betulinic Acid

Produkt 1

HCID 44626706Benzyl betulinateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a suspension of betulinic acid (12 g, 26.3 mmol) and potassium carbonate (7.26 g, 52.6 mmol) in DMF (150 mL) was added benzyl bromide (3.28 mL, 27.6 mmol). The mixture was heated to 60° C. for 3.5 h, and was cooled to rt. Solids started to precipitate upon cooling. The mixture was diluted with 200 mL of water and the solids that formed were collected by filtration to give (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-benzyl 9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylate (13.92 g, 25.5 mmol, 97% yield) as a white solid. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.39-7.28 (m, 5H), 5.16-5.06 (m, 2H), 4.71 (d, J=1.83 Hz, 1H), 4.59 (s, 1H), 3.17 (ddd, J=11.44, 5.65, 5.49 Hz, 1H), 3.01 (td, J=10.99, 4.88 Hz, 1H), 2.27 (ddd, J=12.36, 3.20, 3.05 Hz, 1H), 2.21-2.13 (m, 1H), 1.93-1.81 (m, 2H), 1.67 (s, 3H), 0.95 (s, 3H), 0.93 (s, 3H), 1.71-0.82 (m, 20H), 0.79 (s, 3H), 0.75 (s, 3H), 0.74 (s, 3H).

Aufarbeitung

  1. temperaturewas cooled to rt
  2. customto precipitate
  3. temperatureupon cooling
  4. additionThe mixture was diluted with 200 mL of water
  5. customthe solids that formed
  6. filtrationwere collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-3971812a53f54cee865dc2e68a43982c
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802661B2

Notizen zur Reaktion

Wird geladen…