Pyridine → HCID 89442811, compound

HRID 1474607Notes

Reaction equation

HRID 1474607 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]([O:33][CH2:34][CH:35]=O)=[CH:29][CH:28]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:37][O:38][C:39](=[O:41])[CH3:40])(=[O:3])[CH3:2].N1C=CC=CC=1.C([O-])(=O)C.[Na+].Cl.[CH3:54][O:55][NH2:56]>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]([O:33][CH2:34][CH:35]=[N:56][O:55][CH3:54])=[CH:31][CH:32]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:37][O:38][C:39](=[O:41])[CH3:40])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 89442768HCID 89442768, compound

Product 1

HCID 89442811HCID 89442811, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(2-oxoethoxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (145 mg, 0.25 mmol), in ethanol (10 mL) under nitrogen atmosphere, were added pyridine (0.099 mL, 1.28 mmol), sodium acetate (201.3 mg, 2.45 mmol) and O-methylhydroxylamine hydrochloride (102 mg, 1.22 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 (50 mL). The organic layer was separated, washed with water (2×10 mL), dried over Na2SO4 and concentrated in vacuo to afford crude product which was purified by column chromatography (silica gel, 1.8:8.2 Acetone:Pet. Ether) to afford title compound (100 mg, 64.4%).

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 (50 mL)
  5. customThe organic layer was separated
  6. washwashed with water (2×10 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, 1.8:8.2 Acetone:Pet. Ether)

Sources & evidence

ORD record
ord-c8425088aa484728ab9321d0eb7a0218
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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