Pyridine → HCID 131723973, compound

HRID 1357501Notes

Reaction equation

HRID 1357501 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][C@:11]1([C:23]([O:25][CH3:26])=[O:24])[CH2:21][C@@H:20]([OH:22])[C@@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@@H:13]2[CH2:12]1.N1C=CC=CC=1>ClCCl>[C:1]([O:22][C@H:20]1[C@@H:14]2[O:15][C:16]([CH3:18])([CH3:19])[O:17][C@@H:13]2[CH2:12][C@@:11]([OH:10])([C:23]([O:25][CH3:26])=[O:24])[CH2:21]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 11680350HCID 11680350, compound

Product 1

HCID 131723973HCID 131723973, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (0.78 mL, 6.7 mmol) was added dropwise to 0° C. a solution of Example 13B (1.65 g, 6.7 mmol) and pyridine (0.82 mL, 10.1 mmol) in dichloromethane (40 mL). After stirring for 12 hours, the reaction mixture was washed with aqueous HCl (2N), saturated NaHCO3 solution, and brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by flash chromatography using hexanes/ethyl acetate (3/2) to afford 2.02 g (86%) of the desired product as a white solid.

Workup

  1. washthe reaction mixture was washed with aqueous HCl (2N), saturated NaHCO3 solution, and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash chromatography

Sources & evidence

ORD record
ord-1f61b840ec1e489db1d90cdebdf3399a
Source dataset
uspto-grants-2003_07
Patent number
US06593314B1

Reaction notes

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