Galactaric acid → HCID 131723458, compound

HRID 2305406Notes

Reaction equation

HRID 2305406 reaction equation
[N:1]1[CH:6]=[C:5]([C@@:7]23[CH2:13][C@H:10]([NH:11][CH2:12]2)[CH2:9][NH:8]3)[CH:4]=[N:3][CH:2]=1.[C@H:14]([OH:27])([C@H:22]([OH:26])[C:23]([OH:25])=[O:24])[C@H:15]([OH:21])[C@@H:16]([OH:20])[C:17]([OH:19])=[O:18]>CO.O>[O:18]=[C:17]([OH:19])[C@@H:16]([C@H:15]([C@H:14]([C@@H:22]([C:23]([OH:25])=[O:24])[OH:26])[OH:27])[OH:21])[OH:20].[N:1]1[CH:6]=[C:5]([C@@:7]23[CH2:13][C@H:10]([NH:11][CH2:12]2)[CH2:9][NH:8]3)[CH:4]=[N:3][CH:2]=1.[N:1]1[CH:6]=[C:5]([C@@:7]23[CH2:13][C@H:10]([NH:11][CH2:12]2)[CH2:9][NH:8]3)[CH:4]=[N:3][CH:2]=1

Participants

5

Reactant 2

HCID 3037582Galactaric acidHCID 70163162HCID 70163162, compound

Product 1

HCID 131723458HCID 131723458, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of (1S,4S)-(5-pyrimidinyl)-2,5-diazabicyclo[2.2.1]heptane (0.15 g, 0.851 mmol) in methanol (3 mL) and water (3 mL) was heated at 60° C. as mucic acid (0.09 g, 0.425 mmol) was added. The mixture was heated for 30 min. then filtered through glass wool and concentrated to approximately 1 mL. The treated with diethyl ether (5 mL), then the precipitate was collected, washed with diethyl ether (1 mL) and dried at 45° C. for 4 h to afford (0.142 g, 59%) of white solid, mp 152-172° C. (d).

Workup

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

Sources & evidence

ORD record
ord-8d59ba69950e4f9aaba18b5a6f2acfd8
Source dataset
uspto-grants-2002_08
Patent number
US06440970B1

Reaction notes

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