Betulinic Acid → Boc-Gly betulinic acid

HRID 413660

反応式

HRID 413660 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 131723899Boc-Gly betulinic acid収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-886f198128f14fa6bf1d877958998e50
出典データセット
uspto-grants-2003_05
特許番号
US06569842B2

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