Galactaric acid → HCID 131728242, compound

HRID 2354465Notes

Reaction equation

HRID 2354465 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[O:6][C:7]1[CH:8]=[C:9]([N:13]2[CH2:18][C@@H:17]3[CH2:19][C@H:14]2[CH2:15][NH:16]3)[CH:10]=[N:11][CH:12]=1.[C@H:23]([OH:36])([C@H:31]([OH:35])[C:32]([OH:34])=[O:33])[C@H:24]([OH:30])[C@@H:25]([OH:29])[C:26]([OH:28])=[O:27]>C(O)C.O>[O:27]=[C:26]([OH:28])[C@@H:25]([C@H:24]([C@H:23]([C@@H:31]([C:32]([OH:34])=[O:33])[OH:35])[OH:36])[OH:30])[OH:29].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[O:6][C:7]1[CH:8]=[C:9]([N:13]2[CH2:18][C@@H:17]3[CH2:19][C@H:14]2[CH2:15][NH:16]3)[CH:10]=[N:11][CH:12]=1.[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[O:6][C:7]1[CH:8]=[C:9]([N:13]2[CH2:18][C@@H:17]3[CH2:19][C@H:14]2[CH2:15][NH:16]3)[CH:10]=[N:11][CH:12]=1

Participants

5

Reactant 2

HCID 3037582Galactaric acidHCID 68456377HCID 68456377, compound

Product 1

HCID 131728242HCID 131728242, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of (1S,4S)-2-(5-(3-methoxyphenoxy)-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane (0.23 g, 0.70 mmol) in ethanol (3 mL) and water (2 mL) was heated at 60° C. as mucic acid (0.069 g, 0.33 mmol) was added. The mixture was heated for 30 min, then filtered through glass wool and concentrated to approximately 1 mL. The solution was added dropwise to acetone (12 mL). The precipitate was collected, washed with diethyl ether (2 mL) and dried at 45° C. for 4 h to afford 0.200 g (65%) of fine white crystals; m.p. 172° C. (d).

Workup

  1. additionwas added
  2. temperatureThe mixture was heated for 30 min
  3. filtrationfiltered through glass wool
  4. concentrationconcentrated to approximately 1 mL
  5. additionThe solution was added dropwise to acetone (12 mL)
  6. customThe precipitate was collected
  7. washwashed with diethyl ether (2 mL)
  8. customdried at 45° C. for 4 h

Sources & evidence

ORD record
ord-1e3c14c050eb44a587862513fa3ff439
Source dataset
uspto-grants-2010_07
Patent number
USRE041439E1

Reaction notes

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