Hydrochloric Acid → HCID 22616364, compound

HRID 842954Notes

Reaction equation

HRID 842954 reaction equation
[C:1]([C:3]([C:16]1[C:24]2[O:23][C:22]([CH3:26])([CH3:25])[O:21][C:20]=2[C:19]([O:27][CH3:28])=[CH:18][CH:17]=1)([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH2:4][CH2:5][C:6](OC)=[O:7])#[N:2].[H-].[Na+].Cl>COCCOC>[C:1]([C:3]1([C:16]2[C:24]3[O:23][C:22]([CH3:26])([CH3:25])[O:21][C:20]=3[C:19]([O:27][CH3:28])=[CH:18][CH:17]=2)[CH2:4][CH2:5][C:6](=[O:7])[CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:10]1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 22616353HCID 22616353, compound

Product 1

HCID 22616364HCID 22616364, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of Compound 12b (11 g, 27 mmol) obtained in Step B in 1,2-dimethoxyethane (161 mL) was added 60% sodium hydride (3.3 g, 83 mmol). After refluxing for 3 hours, the mixture was allowed to cool and poured into ice water, and the mixture was acidified with 6 mol/L hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=3/1) to give Compound 12c (8.4 g, 86%) as a white solid.

Workup

  1. temperatureAfter refluxing for 3 hours
  2. temperatureto cool
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography (eluted with hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-e8273eab754746f59696a16c8ab7b808
Source dataset
uspto-grants-2002_04
Patent number
US06376535B2

Reaction notes

Loading…