HCID 66664091, compound → HCID 59841051, compound

HRID 1625157Notes

Reaction equation

HRID 1625157 reaction equation
[CH3:1][CH:2]([O:27][C:28](=[O:30])[CH3:29])[C:3](=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[C:18](=[O:26])[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)N1CCCCC1>C(#N)C>[CH3:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]2[C:12]=1[C:18](=[O:26])[N:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:3]([CH:2]([O:27][C:28](=[O:30])[CH3:29])[CH3:1])=[N:10]2

Participants

3

Reactant 1

HCID 66664091HCID 66664091, compound

Product 1

HCID 59841051HCID 59841051, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 179 (0.037 g, 0.09 mmol) was dissolved in acetonitrile (10 mL) and the reaction mixture was heated at reflux for 3 h. The solvent was removed under reduced pressure and the residue dissolved in a mixture of ethyl acetate (10 mL) and 1M HCl (5 mL). After separating the aqueous layer, the organic layer was washed with additional 1M HCl (2×5 mL), saturated sodium bicarbonate solution (3×5 mL), water (2×5 mL) and saturated brine (5 mL). The solution was dried (MgSO4), filtered, and the filtrate concentrated under reduced pressure to give compound 180. ESI-MS m/z=323 (MH+). The product had nearly totally racemized at this point (chiral purity was 46:54 S:R). The reaction described above and compound 180 are shown below.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue dissolved in a mixture of ethyl acetate (10 mL) and 1M HCl (5 mL)
  5. customAfter separating the aqueous layer
  6. washthe organic layer was washed with additional 1M HCl (2×5 mL), saturated sodium bicarbonate solution (3×5 mL), water (2×5 mL) and saturated brine (5 mL)
  7. dry with materialThe solution was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-8508443cbf064ff79ea4c27b4e24d223
Source dataset
uspto-grants-2014_07
Patent number
US08779131B2

Reaction notes

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