Hydrogen Bromide → Methyl 3alpha-acetoxy-6-bromo-7-keto-5beta-cholanoate

HRID 1682176ノート

反応式

HRID 1682176 の反応式
[C:1]([O:4][C@@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@H:7]([CH2:8][C:9](=[O:32])[C@@H:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:31])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:6]1)(=[O:3])[CH3:2].[Br:33]Br.Br.O>C(O)(=O)C>[C:1]([O:4][C@@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@H:7]([CH:8]([Br:33])[C:9](=[O:32])[C@@H:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:31])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:6]1)(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 260Hydrogen BromideHCID 962WaterHCID 24408BromineHCID 18647600Cholan-24-oic acid, 3-(acetyloxy)-7-oxo-, methyl ester, (3alpha,5beta)-

生成物 1

HCID 18647599Methyl 3alpha-acetoxy-6-bromo-7-keto-5beta-cholanoate

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

A solution of methyl 3α-acetoxy-7-keto-5β-cholanoate. (5.6 g, 12.54 mmoles) in acetic acid (100 ml) was added with a bromine solution (2.8g) in acetic acid (10 ml) and immediately after with 48% hydrobromic acid (0.74 ml). The resulting reaction mixture was left to react overnight under strong magnetic stirring, then it was poured into water (300 ml) and filtered under vacuum to obtain a solid (8,03 g) which was subjected to flash chromatography on silica, eluting with methylene chloride/methanol 99.5:0.5, to yield 6.0 g of a pure product (91%).

後処理

  1. customThe resulting reaction mixture
  2. waitwas left
  3. customto react overnight under strong magnetic stirring
  4. filtrationfiltered under vacuum

出典と根拠

ORDレコード
ord-bf6697ebe2a2450d9bf465d869383d56
出典データセット
uspto-grants-1992_12
特許番号
US05175320

反応ノート

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