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Benzyl Bromide → 28-O-benzyldihydrobetulinic acid

HRID 2405501
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HRID 2405501 반응식
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]3([CH3:31])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:30])[CH2:9][CH2:10][C@@:11]3([C:27]([OH:29])=[O:28])[CH2:23][CH2:22][C@@H:21]([CH:24]([CH3:26])[CH3:25])[C@@H:12]32)[C:3]1([CH3:33])[CH3:32].C(=O)([O-])[O-].[K+].[K+].Br[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>CN(C=O)C>[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@:7]3([CH3:31])[C@@H:16]2[CH2:15][CH2:14][C@H:13]2[C@@:8]3([CH3:30])[CH2:9][CH2:10][C@@:11]3([C:27]([O:29][CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[O:28])[CH2:23][CH2:22][C@@H:21]([CH:24]([CH3:26])[CH3:25])[C@@H:12]32)[C:3]1([CH3:32])[CH3:33]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 65319Dihydrobetulinic Acid

생성물 1

HCID 46740128-O-benzyldihydrobetulinic acid수율 92%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a solution of (1S,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid (3 g, 6.54 mmol) and potassium carbonate (1.808 g, 13.08 mmol) in DMF (60 mL) was added (bromomethyl)benzene (0.816 mL, 6.87 mmol). The reaction mixture was heated up to 60° C. for 3 h. LCMS indicated the starting material was consumed. The reaction mixture was quenched with 60 ml water, a white precipitate was observed. The white solid was collected through filtration and washed with distilled water. The solid was dried in the air to provide the title compound as white solid (3.3 g, 92%). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.42-7.28 (m, 5H), 5.27-5.01 (m, 2H), 3.18 (dt, J=11.22, 5.53 Hz, 1H), 2.40-2.09 (m, 3H), 1.91-1.73 (m, 2H), 1.72-0.78 (m, 21H), 0.95 (s, 3H), 0.91 (s, 3H), 0.84 (d, J=7.02 Hz, 3H), 0.80 (s, 3H), 0.75 (s, 3H), 0.73 (s, 3H), 0.73 (d, J=6.71 Hz, 3H).

후처리

  1. customwas consumed
  2. customThe reaction mixture was quenched with 60 ml water
  3. filtrationThe white solid was collected through filtration
  4. washwashed with distilled water
  5. customThe solid was dried in the air

출처 및 근거

ORD 기록
ord-fb6810f2fe6a4f539755cfd288704952
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08802661B2

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