Pyridine → HCID 131723889, compound

HRID 412860Notes

Reaction equation

HRID 412860 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([OH:15])[C@@H:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:12]([CH2:24][OH:25])[O:11][C@H:10]1[O:26][CH2:27][C@H:28]([CH2:44][O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:66](Cl)(=[O:71])[C:67]([CH3:70])([CH3:69])[CH3:68]>C(OCC)(=O)C>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([OH:15])[C@@H:13]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@@H:12]([CH2:24][O:25][C:66](=[O:71])[C:67]([CH3:70])([CH3:69])[CH3:68])[O:11][C@H:10]1[O:26][CH2:27][C@H:28]([CH2:44][O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chloride2×HCID 131723887HCID 131723887, compound

Product 1

HCID 131723889HCID 131723889, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-5 °C

Procedure

Compound 6 (687 mg, 0.831 mmol) was dissolved by addition of pyridine (12 mL). Pivaloyl chloride (130 μl, 1.08 mmol) was added to the solution, and the mixture was stirred at −5° C. for 1 hour. Pivaloyl chloride (130 μl, 1.08 mmol) was further added thereto, and the mixture was stirred at −5° C. for 1 hour. The reaction mixture was diluted with ethyl acetate, then filtered through Celite, and 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 7 (716.6 mg, 94.7%).

Workup

  1. stirringthe mixture was stirred at −5° C. for 1 hour
  2. filtrationfiltered through Celite
  3. washwashed 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-98a0a06c99bf452581b8aeb0467b5f0c
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

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