Pyridine → HCID 58392447, compound

HRID 561512Notes

Reaction equation

HRID 561512 reaction equation
N1C=CC=CC=1.[F:7][C:8]1([F:23])[CH2:10][CH:9]1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)[OH:12].[C:24](OC(=O)C)(=[O:26])[CH3:25].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[C:24]([O:12][CH:11]([CH:9]1[CH2:10][C:8]1([F:23])[F:7])[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][CH:14]=1)(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 58392207HCID 58392207, compound

Product 1

HCID 58392447HCID 58392447, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.23 ml (2.86 mmol) of pyridine was added dropwise to 2.40 g (9.52 mmol) of the compound from Example 190A and 1.94 g (19.0 mmol) of acetic anhydride, and the mixture was stirred at RT overnight. The reaction mixture was then added to ethyl acetate and saturated aqueous sodium bicarbonate solution. The phases were separated, and the organic phase was concentrated, and the crude product was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 6/1). 2.66 g (95% of theory) of the title compound were obtained as mixture of diastereomers.

Workup

  1. customThe phases were separated
  2. concentrationthe organic phase was concentrated
  3. customthe crude product was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 6/1)

Sources & evidence

ORD record
ord-c95ea02cf5744536807ea325b3eb6db1
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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