Hydrochloric Acid → HCID 15480787, compound

HRID 842946Notes

Reaction equation

HRID 842946 reaction equation
[C:1]([C:3]([C:16]1[C:25]2[O:24][CH2:23][CH2:22][O:21][C:20]=2[C:19]([O:26][CH3:27])=[CH:18][CH:17]=1)([CH2:10][CH2:11][C:12](OC)=[O:13])[CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])#[N:2].[H-].[Na+].Cl>COCCOC>[C:1]([C:3]1([C:16]2[C:25]3[O:24][CH2:23][CH2:22][O:21][C:20]=3[C:19]([O:26][CH3:27])=[CH:18][CH:17]=2)[CH2:10][CH2:11][C:12](=[O:13])[CH:5]([C:6]([O:8][CH3:9])=[O:7])[CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 15480786HCID 15480786, compound

Product 1

HCID 15480787HCID 15480787, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of Compound 1b (6.4 g, 17 mmol) obtained in Step B in 1,2-dimethoxyethane (96 mL) was added 60% sodium hydride (2.0 g, 50 mmol). After refluxing for 3 hours, the mixture was allowed to cool, poured into ice water, 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=2/1) to give Compound 1c (5.0 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=2/1)

Sources & evidence

ORD record
ord-04129450d5aa4340a7b2c70b87866a33
Source dataset
uspto-grants-2002_04
Patent number
US06376535B2

Reaction notes

Loading…