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

HRID 1682176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1682176
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-bf6697ebe2a2450d9bf465d869383d56
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05175320

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