Pyridine → HCID 54382137, compound

HRID 412862Notes

Reaction equation

HRID 412862 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:23]([OH:24])[C@@H:22]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:21]([CH2:33][OH:34])[O:20][C@H:10]1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:41](Cl)(=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43]>C(OCC)(=O)C>[CH2:1]([O:8][C@@H:9]1[C@@H:23]([OH:24])[C@@H:22]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@@H:21]([CH2:33][O:34][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[O:20][C@H:10]1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chloride2×HCID 53905125HCID 53905125, compound

Product 1

HCID 54382137HCID 54382137, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-5 °C

Procedure

Compound 16 (569 mg, 1.20 mmol) was dissolved by addition of pyridine (17 mL). Pivaloyl chloride (188 μl, 1.57 mmol) was added to the solution, and the mixture was stirred at −5° C. for 1 hour. Pivaloyl chloride (188 μl, 1.57 mmol) was further added thereto, and the mixture was stirred at −5° C. for 1 hour. The reaction mixture was diluted with ethyl acetate, and filtered through Celite, and the filtrate was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine. The ethyl acetate layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (toluene:AcOEt=10:1) to obtain Compound 17 (648 mg, 96.7%).

Workup

  1. stirringthe mixture was stirred at −5° C. for 1 hour
  2. filtrationfiltered through Celite
  3. washthe filtrate was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  4. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (toluene:AcOEt=10:1)

Sources & evidence

ORD record
ord-edf17de53a7748759e3683aa85cc2bfd
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

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