HCID 69411642, compound → HCID 69411353, compound

HRID 1816476Notes

Reaction equation

HRID 1816476 reaction equation
[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C@H:11]([C:12]3[C@H:22]([CH2:23][CH2:24]2)[C@:20]2([CH3:21])[C:15]([C:16]([CH3:36])([CH3:35])[C@@H:17]([O:27][Si](C(C)(C)C)(C)C)[CH2:18][CH2:19]2)=[CH:14][CH:13]=3)[CH2:10][CH2:9]1)[CH3:7]>CO.Cl>[CH3:1][O:2][C:3](=[O:37])[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C:11]([C:12]3[CH2:13][CH2:14][C@@H:15]4[C@:20]([C:22]=3[CH2:23][CH2:24]2)([CH3:21])[CH2:19][CH2:18][C@H:17]([OH:27])[C:16]4([CH3:36])[CH3:35])=[CH:10][CH2:9]1)[CH3:7]

Participants

4

Reactant 1

HCID 69411642HCID 69411642, compound

Product 1

HCID 69411353HCID 69411353, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethylchola-5,7-dien-24-oic acid methyl ester (1.0 g) is suspended in a mixture of 25 ml methanol and 3.4 ml of concentrated hydrogen chloride acid and refluxed overnight. After evaporation to dryness under reduced pressure the remanens is triturated with methanol and thereafter recrystallized with methanol/water to give the title compound (0.47 g). Melting point: 156-157° C. 1H-NMR (CDCl3, 400 MHz): δ=5.36 (1H, s) 3.67 (3H, s); 3.23 (1H, m). MS (abbreviation for mass spectroscopy): Calculated: 414.6. Found 414.3.

Workup

  1. temperaturerefluxed overnight
  2. customAfter evaporation to dryness under reduced pressure the remanens
  3. customis triturated with methanol
  4. customrecrystallized with methanol/water

Sources & evidence

ORD record
ord-e43e1bfffe8e401ab79d8d9cbbdc13bb
Source dataset
uspto-grants-2005_04
Patent number
US06884796B2

Reaction notes

Loading…