Benzyl Bromide → Benzyl betulinate

HRID 406862

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HRID 406862 반응식
[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]

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 64971Betulinic Acid

생성물 1

HCID 44626706Benzyl betulinate수율 97%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b836702e3c784f52b6d1dde715ce9750
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754068B2

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