HCID 22100392, compound → HCID 178441435, compound

HRID 1457777Notes

Reaction equation

HRID 1457777 reaction equation
[CH2:1]([C:5]1[N:21](CC(=O)C2C=CC=CC=2)[C:8]2=[N:9][C:10]([CH2:19][OH:20])=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C.CO.[Zn]>[CH2:1]([C:5]1[NH:21][C:8]2=[N:9][C:10]([CH2:19][OH:20])=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 1

HCID 22100392HCID 22100392, compound

Product 1

HCID 178441435HCID 178441435, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

4 g(0.010 mole) of the compound obtained in step 8 was dissolved in a mixture of 40 ml of acetic acid and 40 ml of methanol and to the resulting solution was added 13.1 g(0.0002 mole) of zinc powder. The resultant was stirred under ultrasonification for 4 hours, filtered and washed with acetic acid(10 ml×3). To the filtrate was added 50 ml of saturated aqueous ethylene diamine tetraacetic acid solution and then the resultant was stirred for 10 minutes. After adding 100 ml of ethyl acetate, the solution was filtered and washed with 100 ml of aqueous 10% NaHCO3 solution. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified with column chromatography(CH2Cl2 → 10% MeOH/CH2Cl2) to obtain 2.4 g of the title compound(yield 86%).

Workup

  1. filtrationfiltered
  2. washwashed with acetic acid(10 ml×3)
  3. additionTo the filtrate was added 50 ml of saturated aqueous ethylene diamine tetraacetic acid solution
  4. stirringthe resultant was stirred for 10 minutes
  5. additionAfter adding 100 ml of ethyl acetate
  6. filtrationthe solution was filtered
  7. washwashed with 100 ml of aqueous 10% NaHCO3 solution
  8. dry with materialThe organic layer was dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified with column chromatography(CH2Cl2 → 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-1fa3584e2afb4ee2a980c1b2c7b1f8a8
Source dataset
uspto-grants-1998_12
Patent number
US05849753

Reaction notes

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