Pyridine → HCID 131732776, compound

HRID 1474651Notes

Reaction equation

HRID 1474651 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]([C:25]#[N:26])=[C:21]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH:36]=O)=[CH:30][CH:29]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:38][O:39][C:40](=[O:42])[CH3:41])(=[O:3])[CH3:2].N1C=CC=CC=1.Cl.[CH3:50][O:51][NH2:52]>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]([C:25]#[N:26])=[C:21]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH:36]=[N:52][O:51][CH3:50])=[CH:30][CH:29]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:38][O:39][C:40](=[O:42])[CH3:41])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 117761404HCID 117761404, compound

Product 1

HCID 131732776HCID 131732776, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-cyano-3-(4-(2-oxoethoxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (100.0 mg, 0.17 mmol) in ethanol (4 mL) under nitrogen atmosphere, was added pyridine (0.07 mL, 0.86 mmol) and O-methylhydroxylamine hydrochloride (28.7 mg, 0.34 mmol). The reaction mixture was heated at 80° C. for 2 h. After completion of the reaction as confirmed by TLC, the solvent was evaporated. The crude compound was diluted with ethyl acetate (40 mL). The organic layer was separated, washed with 5% HCl (10 mL), water (10 mL), dried over Na2SO4 and concentrated in vacuo to afford crude product which was purified by column chromatography (silica gel, 1:49 EtOAc:Pet Ether) to afford title compound (60 mg, 43%) as solid.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. additionThe crude compound was diluted with ethyl acetate (40 mL)
  4. customThe organic layer was separated
  5. washwashed with 5% HCl (10 mL), water (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, 1:49 EtOAc:Pet Ether)

Sources & evidence

ORD record
ord-de35c2907f824c8b8bb02a5aa11c7f0b
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

Loading…