Glyoxal → HCID 58124001, compound

HRID 1519205Notes

Reaction equation

HRID 1519205 reaction equation
[CH:1]([CH:3]=O)=O.[NH2:5][C:6]1[C:27]([NH2:28])=[CH:26][C:9]2[CH2:10][C@@H:11]3[C:16]([CH3:18])([CH3:17])[C@:15]([CH3:19])([C:8]=2[CH:7]=1)[CH2:14][CH2:13][N:12]3C(=O)C(F)(F)F>C(O)C>[CH3:19][C@@:15]12[C:16]([CH3:18])([CH3:17])[C@@H:11]([CH2:10][C:9]3[CH:26]=[C:27]4[N:28]=[CH:1][CH:3]=[N:5][C:6]4=[CH:7][C:8]=31)[NH:12][CH2:13][CH2:14]2

Participants

4

Reactant 2

HCID 7860GlyoxalHCID 58123670HCID 58123670, compound

Product 1

HCID 58124001HCID 58124001, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Glyoxal (40% in water, 95 μL) is added to 1-[(2R,6S)-8,9-diamino-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl]-2,2,2-trifluoro-ethanone (260 mg) dissolved in ethanol (3 mL) and chilled in an ice bath. The cooling bath is removed and the solution is stirred at ambient temperature overnight. Then, the solution is concentrated and the residue is taken up in methanol (1 mL) and treated with 4 M aqueous NaOH solution (0.38 mL). After stirring at ambient temperature overnight, brine is added and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are washed with brine, dried (MgSO4), and the solvent is removed under reduced pressure to give the crude title compound that is used without further purification.

Workup

  1. temperaturechilled in an ice bath
  2. customThe cooling bath is removed
  3. concentrationThen, the solution is concentrated
  4. additiontreated with 4 M aqueous NaOH solution (0.38 mL)
  5. stirringAfter stirring at ambient temperature overnight
  6. additionbrine is added
  7. extractionthe resulting mixture is extracted with ethyl acetate
  8. washThe combined organic extracts are washed with brine
  9. dry with materialdried (MgSO4)
  10. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-ce357dd484b34ff6acc1591c8c48b3a2
Source dataset
uspto-grants-2015_07
Patent number
US09073870B2

Reaction notes

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