Hydrochloric Acid → HCID 136397323, compound

HRID 2387409Notes

Reaction equation

HRID 2387409 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH3:29])[O:10][CH2:9][CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][N:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25]COC)=[CH:21][CH:20]=2)[CH3:18])[CH2:7][O:6]1)=[O:4].Cl>C(O)(C)C>[CH3:1][O:2][C:3]([C:5]1([CH3:29])[O:10][CH2:9][CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][N:16]=[C:17]([C:19]2[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)[CH3:18])[CH2:7][O:6]1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86648422HCID 86648422, compound

Product 1

HCID 136397323HCID 136397323, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Methyl-5-{4-[1-(4-methoxymethoxy-phenyl)-ethylideneaminooxy]-butyl}-2-methyl-[1,3]dioxane-2-carboxylate (prepared as per example 39) (1.5 g) in isopropyl alcohol was added concentrated hydrochloric acid and the reaction mixture was stirred at 50° C. for about 20 hours. Reaction mixture was cooled to ambient temperature and solvent was evaporated under reduced pressure on a rotavapor. Water was added to the residue and extracted with ethyl acetate. The combined organic extract was washed with water, brine solution, dried over sodium sulphate and evaporated under reduced pressure on a rotavapor. Crude product was flash chromatographed over silica gel using 15% ethyl acetate in petroleum ether as eluent to obtain 200 mg of pure product.

Workup

  1. customReaction mixture
  2. temperaturewas cooled to ambient temperature
  3. customsolvent was evaporated under reduced pressure on a rotavapor
  4. additionWater was added to the residue
  5. extractionextracted with ethyl acetate
  6. extractionThe combined organic extract
  7. washwas washed with water, brine solution
  8. dry with materialdried over sodium sulphate
  9. customevaporated under reduced pressure on a rotavapor
  10. customchromatographed over silica gel using 15% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-4e2b539dbe9640b08b4e57300e2c65f7
Source dataset
uspto-grants-2012_09
Patent number
US08268867B2

Reaction notes

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