Pyridine → HCID 117761411, compound

HRID 1474648Notes

Reaction equation

HRID 1474648 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[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]([C:33]4([CH:36]=O)[CH2:35][CH2:34]4)=[CH:29][CH:28]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:38][O:39]C(=O)C)(=O)C.N1C=CC=CC=1.Cl.[CH3:50][O:51][NH2:52]>C(O)C>[CH3:50][O:51][N:52]=[CH:36][C:33]1([C:30]2[CH:31]=[CH:32][C:27]([CH2:26][C:21]3[CH:20]=[C:19]([C@H:8]4[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:38][OH:39])[O:7]4)[CH:24]=[CH:23][C:22]=3[Cl:25])=[CH:28][CH:29]=2)[CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 89442827HCID 89442827, compound

Product 1

HCID 117761411HCID 117761411, compoundYield 118.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(1-formylcyclopropyl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (300.0 mg, 0.44 mmol), in ethanol (5 mL) under nitrogen atmosphere, was added pyridine (0.17 mL, 2.20 mmol) and O-methylhydroxylamine hydrochloride (73.0 mg, 0.88 mmol). The reaction mixture was heated at 80° C. for 4 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 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, 1:4 EtOAc:Pet Ether) to afford the title compound (240 mg, 77%) as a white 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. washThe organic layer was washed with 5% HCl (10 mL), water (10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customto afford crude product which
  8. customwas purified by column chromatography (silica gel, 1:4 EtOAc:Pet Ether)

Sources & evidence

ORD record
ord-e2230fd9aa7c4b7db986b6dd14df7baf
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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