Aminoacetaldehyde dimethyl acetal → HCID 22141244, compound

HRID 428927Notes

Reaction equation

HRID 428927 reaction equation
Cl.[CH2:2]([N:8]1[CH2:13][CH:12]2[CH:10]([C:11]2([C:15]2[CH:16]=[C:17]([C:21](=[NH:25])OCC)[CH:18]=[CH:19][CH:20]=2)[CH3:14])[C:9]1=[O:26])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].CO[CH:29](OC)[CH2:30][NH2:31]>CO>[NH3:8].[CH2:2]([N:8]1[CH2:13][CH:12]2[CH:10]([C:11]2([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[NH:31][CH:30]=[CH:29][N:25]=3)[CH:16]=2)[CH3:14])[C:9]1=[O:26])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 22141158HCID 22141158, compound

Product 2

HCID 222AmmoniaHCID 22141244HCID 22141244, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 3-(3-hexyl-6-methyl-2-oxo-3-azabicyclo[3.1.0]hex-6-yl)benzenecarboximidoate hydrochloride (Preparation 42, 528 mg, 1.45 mmol) in methanol (6 ml) at room temperature was added aminoacetaldehyde dimethylacetal (0.16 g, 1.52 mmol). The mixture was heated under reflux for 90 min, cooled to room temperature and the solvent was removed in vacuo. The crude residue was dissolved in 6N hydrochloric acid (8 ml) and the mixture was heated to 80° C. for 30 min and then left at room temperature for 2 h. The mixture was diluted with water (5 ml), the pH was adjusted to 9 using 5N sodium hydroxide solution and the aqueous solution was extracted with ethyl acetate (3×20 ml). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica column chromatography eluting with ethyl acetate:methanol:ammonia solution (0.880) (90:10:1) to afford the title compound (190 mg, 39%) as a colourless oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 90 min
  3. customthe solvent was removed in vacuo
  4. dissolutionThe crude residue was dissolved in 6N hydrochloric acid (8 ml)
  5. temperaturethe mixture was heated to 80° C. for 30 min
  6. additionThe mixture was diluted with water (5 ml)
  7. extractionthe aqueous solution was extracted with ethyl acetate (3×20 ml)
  8. dry with materialThe combined extracts were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude residue was purified by silica column chromatography
  12. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-f74baa6bf2914c72bd8e539f7c5e7064
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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