Benzyl Bromide → Benzyl betulinate

HRID 406862

反応式

HRID 406862 の反応式
[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]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 64971Betulinic Acid

生成物 1

HCID 44626706Benzyl betulinate収率 97%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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 0.74 (s, 3H), 0.75 (s, 3H), 0.79 (s, 3H), 0.82-1.71 (m, 20H), 0.93 (s, 3H), 0.95 (s, 3H), 1.67 (s, 3H), 1.81-1.93 (m, 2H), 2.13-2.21 (m, 1H), 2.27 (ddd, J=12.36, 3.20, 3.05 Hz, 1H), 3.01 (td, J=10.99, 4.88 Hz, 1H), 3.17 (ddd, J=11.44, 5.65, 5.49 Hz, 1H), 4.59 (s, 1H), 4.71 (d, J=1.83 Hz, 1H), 5.06-5.16 (m, 2H), 7.28-7.39 (m, 5H).

後処理

  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

出典と根拠

ORDレコード
ord-b836702e3c784f52b6d1dde715ce9750
出典データセット
uspto-grants-2014_06
特許番号
US08754068B2

関連ノート

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