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Betulinic Acid → Boc-Gly betulinic acid

HRID 413660
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 413660
[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=[O:4].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:25][C:26]([C@H:28]1[C@@H:32]2[C@@H:33]3[C@@:46]([CH3:49])([CH2:47][CH2:48][C@@:31]2([C:55]([OH:57])=[O:56])[CH2:30][CH2:29]1)[C@@:45]1([CH3:50])[C@@H:36]([C@:37]2([CH3:54])[C@@H:42]([CH2:43][CH2:44]1)[C:41]([CH3:52])([CH3:51])[C@@H:40]([OH:53])[CH2:39][CH2:38]2)[CH2:35][CH2:34]3)=[CH2:27]>C1COCC1>[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=[O:4].[CH3:27][C:26]([C@H:28]1[C@@H:32]2[C@@H:33]3[C@@:46]([CH3:49])([CH2:47][CH2:48][C@@:31]2([C:55]([OH:57])=[O:56])[CH2:30][CH2:29]1)[C@@:45]1([CH3:50])[C@@H:36]([C@:37]2([CH3:54])[C@@H:42]([CH2:43][CH2:44]1)[C:41]([CH3:51])([CH3:52])[C@@H:40]([OH:53])[CH2:39][CH2:38]2)[CH2:35][CH2:34]3)=[CH2:25]
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Komponenten

5

Edukt 3

HCID 64971Betulinic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycine

Produkt 1

HCID 131723899Boc-Gly betulinic acidAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of Boc-Gly-OH (525 mg, 3 mmol) in THF (5 ml) was added CDI (486 mg, 3 mmol). The mixture was stirred at room temperature for 2 hours, then betulinic acid (684 mg, 1.5 mmol) was added. The resulting mixture was refluxed overnight. After removal of solvent, the residue was dissolved in dichloromethane, washed with water, followed by brine, and dried over Na2SO4. After removal of solvent, the residue was purified by a column chromatography on silica gel with EtOAc/-hexane as an eluent to give 900 mg of Boc-Gly-betulinic acid derivative (4i). Yield: 97%. m.p.: 135-136° C. 1H NMR (DMSO-d6) δ: 0.75-1.7 (m, 47H), 1.75-1.9 (m, 2H), 2.05-2.3 (m, 2H), 2.9-3.0 (m, 1H), 3.63 (d, J=6 Hz, 2H), 4.4 (m, 1H), 4.56 (d, J=2 Hz, 1H), 4.69 (d, J=2 Hz, 1H), 7.18 (t, J=6 Hz, 1H), 12.05 (s, 1H). MS (ESI−): 612.4 (M-1). FT-IR (cm−1): 2943, 2869, 1702. Anal. Calcd for C37H59N1O6: C, 72.39; H, 9.69; N, 2.28; Found: C, 72.13; H, 10.07; N, 2.20.

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed overnight
  2. customAfter removal of solvent
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customAfter removal of solvent
  7. customthe residue was purified by a column chromatography on silica gel with EtOAc/-hexane as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-886f198128f14fa6bf1d877958998e50
Quelldatensatz
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06569842B2

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