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Benzyl Bromide → 28-O-benzyldihydrobetulinic acid

HRID 2405501
ノート
印刷プレビュー

反応式

HRID 2405501 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 65319Dihydrobetulinic Acid

生成物 1

HCID 46740128-O-benzyldihydrobetulinic acid収率 92%

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 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).

後処理

  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

出典と根拠

ORDレコード
ord-fb6810f2fe6a4f539755cfd288704952
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08802661B2

反応ノート

読み込み中…

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