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

HRID 346117노트

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HRID 346117 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 18647599Methyl 3alpha-acetoxy-6-bromo-7-keto-5beta-cholanoate수율 121.9%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-e8eac05165e34a028344bf7578c8875b
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05061701

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