Pyridine → HCID 89442828, compound

HRID 1474628Notes

Reaction equation

HRID 1474628 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH:34]=O)=[CH:29][CH:28]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:36][O:37][C:38](=[O:40])[CH3:39])(=[O:3])[CH3:2].N1C=CC=CC=1.Cl.[CH3:48][O:49][NH2:50]>C(O)C>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([CH2:33][CH:34]=[N:50][O:49][CH3:48])=[CH:31][CH:32]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:36][O:37][C:38](=[O:40])[CH3:39])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 89442804HCID 89442804, compound

Product 1

HCID 89442828HCID 89442828, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2R,3 R,4R,5S,65)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(2-oxoethyl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (0.35 mg, 0.61 mmol), in ethanol (10 mL) under nitrogen atmosphere, were added pyridine (0.24 mL, 3.04 mmol), and O-methylhydroxylamine hydrochloride (151 mg, 1.82 mmol). The reaction mixture was refluxed for 2 h. After completion of the reaction as confirmed by TLC, the solvent was evaporated. The crude compound was diluted with ethyl acetate (25 mL). The organic layer was washed with water (3×10 mL), dried over Na2SO4 and concentrated in vacuo to afford crude product which was purified by column chromatography (silica gel, 1.0:9.0 Acetone:Pet. Ether) to afford the title compound (80 mg, 22%).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. additionThe crude compound was diluted with ethyl acetate (25 mL)
  5. washThe organic layer was washed with water (3×10 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto afford crude product which
  9. customwas purified by column chromatography (silica gel, 1.0:9.0 Acetone:Pet. Ether)

Sources & evidence

ORD record
ord-57c0f910c83b4824ab1a0bac45b8417f
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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