Galactaric acid → HCID 131723457, compound

HRID 2305405Notes

Reaction equation

HRID 2305405 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([O:7][C:8]2[CH:9]=[C:10]([C@@:14]34[CH2:20][C@H:17]([NH:18][CH2:19]3)[CH2:16][N:15]4[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:11]=[N:12][CH:13]=2)=[CH:5][CH:4]=1.[C@H:30]([OH:43])([C@H:38]([OH:42])[C:39]([OH:41])=[O:40])[C@H:31]([OH:37])[C@@H:32]([OH:36])[C:33]([OH:35])=[O:34]>C(O)C.O>[O:34]=[C:33]([OH:35])[C@@H:32]([C@H:31]([C@H:30]([C@@H:38]([C:39]([OH:41])=[O:40])[OH:42])[OH:43])[OH:37])[OH:36].[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([O:7][C:8]2[CH:9]=[C:10]([C@@:14]34[CH2:20][C@H:17]([NH:18][CH2:19]3)[CH2:16][N:15]4[C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH:11]=[N:12][CH:13]=2)=[CH:5][CH:4]=1.[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([O:7][C:8]2[CH:9]=[C:10]([C@@:14]34[CH2:20][C@H:17]([NH:18][CH2:19]3)[CH2:16][N:15]4[C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH:11]=[N:12][CH:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 3037582Galactaric acidHCID 22965629HCID 22965629, compound

Product 1

HCID 131723457HCID 131723457, compoundYield 338%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of (1S,4S)-(5-(4-methoxyphenoxy)-3-pyridyl)-2-N-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane (0.26 g, 0.87 mmol) in ethanol (2 mL) and water (2 mL) was heated at 60° C. as mucic acid (0.075 g, 0.0574 mmol) was added. The mixture was heated for 30 min then filtered through glass wool and concentrated to approximately 1 mL. The solution was treated with diethyl ether (4 mL). The resulting precipitate was collected, washed with diethyl ether (1 mL) and dried at 45° C. for 4 h. to afford (0.195 g, 68%) of white solid, mp 172-182° 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 solution was treated with diethyl ether (4 mL)
  6. customThe resulting precipitate was collected
  7. washwashed with diethyl ether (1 mL)
  8. customdried at 45° C. for 4 h.

Sources & evidence

ORD record
ord-f0fffd63c04c40c9bf97777d32d459ba
Source dataset
uspto-grants-2002_08
Patent number
US06440970B1

Reaction notes

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