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

HRID 346117ノート

反応式

HRID 346117 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収率 121.9%

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 (2.8 g) 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-e8eac05165e34a028344bf7578c8875b
出典データセット
uspto-grants-1991_10
特許番号
US05061701

反応ノート

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