Pyridine → HCID 131732772, compound

HRID 1474615Notes

Reaction equation

HRID 1474615 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]([O:19][CH3:20])[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH:37]=O)=[CH:31][CH:30]=2)[CH:22]=1)(=[O:3])[CH3:2].N1C=CC=CC=1.C([O-])(=O)C.[Na+].Cl.[CH3:51][O:52][NH2:53]>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]([O:19][CH3:20])[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH:37]=[N:53][O:52][CH3:51])=[CH:31][CH:30]=2)[CH:22]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 89442841HCID 89442841, compound

Product 1

HCID 131732772HCID 131732772, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-(2-oxoethoxy)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (200 mg, 0.365 mmol), in ethanol (10 mL) under nitrogen atmosphere, were added pyridine (0.147 mL, 1.82 mmol), sodium acetate (299 mg, 3.65 mmol) and O-methylhydroxylamine hydrochloride (152 mg, 1.82 mmol). The reaction mixture was refluxed for 5 h. After completion of the reaction as confirmed by TLC, the solvent was evaporated. The crude compound was extracted with ethyl acetate (3×25 mL). The organic layer was separated, 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, 1.5:8.5 Acetone:Pet. Ether) to afford the title compound (140 mg, 64.5%).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. extractionThe crude compound was extracted with ethyl acetate (3×25 mL)
  5. customThe organic layer was separated
  6. washwashed with water (3×10 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customto afford crude product which
  10. customwas purified by column chromatography (silica gel, 1.5:8.5 Acetone:Pet. Ether)

Sources & evidence

ORD record
ord-ca841b3d06a1408790b5603252390593
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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