Acetic Acid → HCID 23447292, compound

HRID 1840549Notes

Reaction equation

HRID 1840549 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:12]1([C:17]2[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=2)[CH:16]=[CH:15][N:14]=[CH:13]1.C(O)(=O)C.C(O[BH-](O[C:39](=[O:41])[CH3:40])OC(=O)C)(=O)C.[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:21][C:20]2[CH:23]=[CH:24][C:17]([N:12]3[CH:16]=[CH:15][N:14]=[CH:13]3)=[CH:18][CH:19]=2)[C:39](=[O:41])[CH2:40]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 187201N-BOC-ethylenediamineHCID 7365304-(1H-imidazol-1-yl)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 23447292HCID 23447292, compoundYield 991.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N— (tert-butoxycarbonyl)ethylenediamine (5.0 g) and 4-(1H-imidazol-1-yl)benzaldehyde (5.35 g) in methanol (10 ml) was added acetic acid (300 mg), and the mixture was stirred at room temperature for 1 hour. To the mixture was added, under ice-cooling, sodium triacetoxyborohydride (318 mg), and the mixture was stirred at room temperature for 5 hours. The reaction solution was concentrated, and the residue was dissolved in ethyl acetate. The solution was extracted with water, and the aqueous layer was made alkaline with sodium hydroxide solution. The mixture was extracted with dichloromethane and dried with sodium sulfate, and sodium sulfate was filtered off. To the filtrate was added triethylamine (6.3 g) and then was added at 0° C. chloroacetyl chloride (3.53 g), and the mixture was stirred at room temperature for 30 minutes. The reaction solution washed with sodium bicarbonate solution and brine, dried and concentrated, and the residue was dissolved in DMF (100 ml). To the solution was added sodium hydride in oil (1.50 g), and the mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated, and the residue was dissolved in ethyl acetate. The solution was washed with water and brine, dried and concentrated, and the residue was purified with column chromatography (ethyl acetate) to give colorless amorphous of the title compound (5.3 g).

Workup

  1. additionTo the mixture was added, under ice-
  2. temperaturecooling
  3. concentrationThe reaction solution was concentrated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. extractionThe solution was extracted with water
  6. extractionThe mixture was extracted with dichloromethane
  7. dry with materialdried with sodium sulfate, and sodium sulfate
  8. filtrationwas filtered off
  9. additionTo the filtrate was added triethylamine (6.3 g)
  10. additionwas added at 0° C. chloroacetyl chloride (3.53 g)
  11. stirringthe mixture was stirred at room temperature for 30 minutes
  12. washThe reaction solution washed with sodium bicarbonate solution and brine
  13. customdried
  14. concentrationconcentrated
  15. dissolutionthe residue was dissolved in DMF (100 ml)
  16. additionTo the solution was added sodium hydride in oil (1.50 g)
  17. stirringthe mixture was stirred at room temperature for 3 hours
  18. concentrationThe reaction solution was concentrated
  19. dissolutionthe residue was dissolved in ethyl acetate
  20. washThe solution was washed with water and brine
  21. customdried
  22. concentrationconcentrated
  23. customthe residue was purified with column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-e52d65f7d0bb40c79fc7cf0e2657eac7
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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