Galactaric acid → (2R)-(4E)-N-Methyl-5-(5-isopropoxy-3-pyridyl)-4-penten-2-amine Hemigalactarate

HRID 968404Notes

Reaction equation

HRID 968404 reaction equation
[O:1]=[C:2]([OH:14])[C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([C:11]([OH:13])=[O:12])[OH:10])[OH:8])[OH:6])[OH:4].[CH3:15][NH:16][C@@H:17]([CH2:19]/[CH:20]=[CH:21]/[C:22]1[CH:23]=[N:24][CH:25]=[C:26]([O:28][CH:29]([CH3:31])[CH3:30])[CH:27]=1)[CH3:18]>CC(O)C.O>[O:1]=[C:2]([OH:14])[C@@H:3]([C@H:5]([C@H:7]([C@@H:9]([C:11]([OH:13])=[O:12])[OH:10])[OH:8])[OH:6])[OH:4].[CH3:15][NH:16][C@@H:17]([CH2:19]/[CH:20]=[CH:21]/[C:22]1[CH:23]=[N:24][CH:25]=[C:26]([O:28][CH:29]([CH3:31])[CH3:30])[CH:27]=1)[CH3:18].[CH3:25][NH:24][C@@H:23]([CH2:11]/[CH:9]=[CH:7]/[C:5]1[CH:15]=[N:16][CH:17]=[C:2]([O:14][CH:20]([CH3:21])[CH3:19])[CH:3]=1)[CH3:22]

Participants

5

Reactant 2

HCID 3037582Galactaric acidHCID 9921040(R,E)-5-(5-Isopropoxypyridin-3-yl)-N-methylpent-4-en-2-amine

Product 1

HCID 131722559(2R)-(4E)-N-Methyl-5-(5-isopropoxy-3-pyridyl)-4-penten-2-amine Hemigalactarate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Conditions

Temperature
60 °C

Procedure

Galactaric acid (314.0 mg, 1.49 mmol) was dissolved in 2-propanol (10 mL) and water (˜1 mL), assisted by heating and sonicating over a period of 10 min. A solution of (2R)-(4E)-N-methyl-5-(5-isopropoxy-3-pyridyl)-4-penten-2-amine (700.3 mg, 2.99 mmol) in 2-propanol (10 mL) was then added, followed by additional sonicating and heating at 60° C. for 10 min. The hot solution was filtered to remove some insoluble material. The solvent was removed on a rotary evaporator; the resulting light-brown syrup was dissolved in dry 2-propanol (5 mL) and cooled at 4° C. The resulting precipitate was filtered and dried under high vacuum to yield 657 mg (64.8%) of an off-white, crystalline powder, mp 150-153° C.

Workup

  1. temperatureby heating
  2. customsonicating over a period of 10 min
  3. customby additional sonicating
  4. filtrationThe hot solution was filtered
  5. customto remove some insoluble material
  6. customThe solvent was removed on a rotary evaporator
  7. dissolutionthe resulting light-brown syrup was dissolved in dry 2-propanol (5 mL)
  8. temperaturecooled at 4° C
  9. filtrationThe resulting precipitate was filtered
  10. customdried under high vacuum
  11. customto yield 657 mg (64.8%) of an off-white, crystalline powder, mp 150-153° C.

Sources & evidence

ORD record
ord-4c083740b13049f6827fcc483d73ec2b
Source dataset
uspto-grants-2005_10
Patent number
US06958399B2

Reaction notes

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