Hydrochloric Acid → HCID 19348478, compound

HRID 1637504Notes

Reaction equation

HRID 1637504 reaction equation
Cl.[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]=[N+]=[N-])=[CH:8][C:7]=1[NH:16][C:17](=[O:35])[CH2:18][CH:19]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[O:33][CH3:34])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])([CH3:5])([CH3:4])[CH3:3]>CC(C)=O.[Zn]>[C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH2:13])=[CH:8][C:7]=1[NH:16][C:17](=[O:35])[CH2:18][CH:19]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[O:33][CH3:34])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])([CH3:3])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19348686HCID 19348686, compound

Product 1

HCID 19348478HCID 19348478, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 180AcetoneSolvent

Procedure

301 mg (4.60 mmol) of zinc dust and then 5 ml of 2 N aqueous hydrochloric acid were added to a solution of 430 mg (0.92 mmol) of N-(2-t-butyl-5-azidomethylphenyl)-3-(2,4-dimethoxyphenyl)octanamide [prepared as described in step (i) above] in 10 ml of acetone, and the resulting mixture was stirred for 1 hour. At the end of this time, the reaction mixture was filtered to remove zinc dust, and the filtrate was made alkaline by adding a saturated aqueous solution of sodium hydrogencarbonate. The mixture was then extracted with ethyl acetate. The extract was washed with water and then with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 50 g of silica gel using a 10:1 by volume mixture of ethyl acetate and ethanol as the eluent, to give 354 mg (yield 86%) of the title compound as a foam-like substance.

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. customto remove zinc dust
  3. additionby adding a saturated aqueous solution of sodium hydrogencarbonate
  4. extractionThe mixture was then extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialwith a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe resulting residue was purified by column chromatography through 50 g of silica gel using a 10:1
  9. additionby volume mixture of ethyl acetate and ethanol as the eluent

Sources & evidence

ORD record
ord-7c3c17e398f24be99fc67fb16ab19226
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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