Pyridine → HCID 57044786, compound

HRID 2298240Notes

Reaction equation

HRID 2298240 reaction equation
[OH2:1].O.O.[F-:4].C([N+:9]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH2:12]C)CCC.N1C=CC=CC=1.[C:28]([O:31][C:32](=O)[CH3:33])(=[O:30])[CH3:29].C1[CH2:39][O:38][CH2:37]C1>>[CH3:37][O:38][C:39]([C:19]1[C:20]2[C:14](=[CH:15][CH:16]=[C:17]([F:4])[CH:21]=2)[N:9]([C@@H:10]2[CH2:33][C@H:32]([O:31][C:28](=[O:30])[CH3:29])[CH:12]=[CH:11]2)[CH:18]=1)=[O:1]

Participants

5

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 11726816Tetrabutylammonium Fluoride Trihydrate

Product 1

HCID 57044786HCID 57044786, compoundYield 96%

Procedure

In a flask was dissolved the compound obtained in Example 3a) (6.1 g, 15.7 mmol), in THF (70 mL). Tetrabutylammonium fluoride trihydrate (9.0 g, 28.5 mmol) was added and the flask was sealed, and stirred at room temperature for 1 hour. The solution was cooled on ice and pyridine (100 mL), and acetic anhydride (50 mL) was added. The ice bath was removed after 30 minutes, and the mixture was stirred at room temperature for another 3 hours. The volatiles were removed in vaccuo and the residue was taken up in ethyl acetate and washed with water, saturated aqueous sodium hydrogen carbonate (10%) and brine. The organic solution was concentrated in vaccuo and the residue was purified on silica (toluene-ethyl acetate, 7:1), giving 4.8 g (96%) of the sub-title compound as a brownish solid.

Workup

  1. customthe flask was sealed
  2. additionwas added
  3. customThe ice bath was removed after 30 minutes
  4. stirringthe mixture was stirred at room temperature for another 3 hours
  5. customThe volatiles were removed in vaccuo
  6. washwashed with water, saturated aqueous sodium hydrogen carbonate (10%) and brine
  7. concentrationThe organic solution was concentrated in vaccuo
  8. customthe residue was purified on silica (toluene-ethyl acetate, 7:1)

Sources & evidence

ORD record
ord-6fb30ef27c524610aa51db1d43b71285
Source dataset
uspto-grants-2002_12
Patent number
US06492406B1

Reaction notes

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