Pivaloyl chloride → HCID 86758967, compound

HRID 412866Notes

Reaction equation

HRID 412866 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:42]([OH:43])[C@@H:41]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C@@H:40]([CH2:52][OH:53])[O:39][C@H:10]1[O:11][CH2:12][CH:13]([CH2:15][CH2:16][CH2:17][C@H:18]([C@@H:20]1[C@:37]2([CH3:38])[C@H:23]([C@H:24]3[C@H:34]([CH2:35][CH2:36]2)[C@:32]2([CH3:33])[CH:27]([CH2:28][CH2:29][CH2:30][CH2:31]2)[CH2:26][CH2:25]3)[CH2:22][CH2:21]1)[CH3:19])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:54](Cl)(=[O:59])[C:55]([CH3:58])([CH3:57])[CH3:56]>N1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C@@H:9]1[C@@H:42]([OH:43])[C@@H:41]([O:44][CH2:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C@@H:40]([CH2:52][O:53][C:54](=[O:59])[C:55]([CH3:58])([CH3:57])[CH3:56])[O:39][C@H:10]1[O:11][CH2:12][CH:13]([CH2:15][CH2:16][CH2:17][C@H:18]([C@@H:20]1[C@:37]2([CH3:38])[C@H:23]([C@H:24]3[C@H:34]([CH2:35][CH2:36]2)[C@:32]2([CH3:33])[CH:27]([CH2:28][CH2:29][CH2:30][CH2:31]2)[CH2:26][CH2:25]3)[CH2:22][CH2:21]1)[CH3:19])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 62493Pivaloyl chloride2×HCID 86758968HCID 86758968, compound

Product 1

HCID 86758967HCID 86758967, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-2.5 °C

Procedure

Compound 26 (647 mg, 0.885 mmol) was dissolved in pyridine (13 mL). To the solution, pivaloyl chloride (138 μl, 1.15 mmol) was added, and the mixture was stirred at −5 to 0° C. for 0.5 hour. Pivaloyl chloride (138 μl, 1.15 mmol) was further added thereto, and the mixture was stirred at −5 to 0° 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 27 (663 mg, 91.9%).

Workup

  1. stirringthe mixture was stirred at −5 to 0° 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-faff2f5d208c4962ac6ccd76a2908b31
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

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