Betulinic Acid → Boc-Gly betulinic acid

HRID 413660

반응식

HRID 413660 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 131723899Boc-Gly betulinic acid수율 97%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-886f198128f14fa6bf1d877958998e50
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06569842B2

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