Ammonium Chloride → HCID 178479636, compound

HRID 487434Notes

Reaction equation

HRID 487434 reaction equation
[CH2:1]([C@H:8]1[C:13](=[O:14])[N:12]([CH2:15][C:16]#[N:17])[CH:11]=[CH:10][N:9]1C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:25]=[N+:26]=[N-:27].[Na+].[Cl-:29].[NH4+]>CN(C)C=O>[ClH:29].[CH2:1]([C@@H:8]1[NH:9][CH2:10][CH2:11][N:12]([CH2:15][C:16]2[NH:17][N:27]=[N:26][N:25]=2)[C:13]1=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 54411304HCID 54411304, compound

Product 1

HCID 178479636HCID 178479636, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.0 g of (S)-2-benzyl-1-t-butoxycarbonyl-4-cyanomethyl-1,2,3,4-tetrahydropyrazin-3-one, 0.31 g of sodium azide, 0.25 g of ammonium chloride and 6 ml of N,N-dimethylformamide was stirred for 6 hours at 100° C. The reaction mixture was poured into ice-water, which was subjected to extraction with methylene chloride. The organic layer was washed with water and dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure. To the solution of 1.0 g of the residue in 15 ml of ethanol was added 0.5 g of 10% palladium-carbon. The mixture was stirred for 20 hours in a hydrogen stream. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. To 1.0 g of the concentrate was added 8 ml of an ethyl acetate solution of 4N HCl, and the mixture was stirred for 3 hours at room temperature. Resulting precipitates were collected by filtration and recrystallized from methanol to afford 0.7 g of the title compound as colorless crystals, m.p.245°-247° C. (decomp.).

Workup

  1. extractionwas subjected to extraction with methylene chloride
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionTo the solution of 1.0 g of the residue in 15 ml of ethanol was added 0.5 g of 10% palladium-carbon
  6. stirringThe mixture was stirred for 20 hours in a hydrogen stream
  7. filtrationThe catalyst was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. additionTo 1.0 g of the concentrate was added 8 ml of an ethyl acetate solution of 4N HCl
  10. stirringthe mixture was stirred for 3 hours at room temperature
  11. customResulting
  12. customprecipitates
  13. filtrationwere collected by filtration
  14. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5fe731ebebb245dbb66af8010becba83
Source dataset
uspto-grants-1994_03
Patent number
US05294713

Reaction notes

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