Pyridine → HCID 86667488, compound

HRID 1847123Notes

Reaction equation

HRID 1847123 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C:13]3[O:14][C:15](=[O:29])[CH:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C:18](=O)[CH2:17]4)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].Cl.[CH3:31][O:32][NH2:33].N1C=CC=CC=1.[Cl-].[NH4+]>C(O)C>[CH3:31][O:32][N:33]=[C:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[CH:16]([C:15](=[O:29])[O:14][C:13]3[C@H:12]4[C@:26]([CH3:27])([CH2:25][CH2:24][C:23]=32)[C@@H:9]([C@@H:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:3])[CH3:1])[CH2:10][CH2:11]4)[CH2:17]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 25517Ammonium ChlorideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 67609998HCID 67609998, compound

Product 1

HCID 86667488HCID 86667488, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 1 (40 mg, 0.10 mmol) obtained in Example 1 was dissolved in ethanol (5 mL), and O-methylhydroxyamine hydrochloride (25 mg, 0.30 mmol) and pyridine (0.024 mL, 0.03 mmol) were added thereto, followed by stirring at room temperature for 3 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate twice. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to yield a residue. The residue was purified by preparative thin layer chromatography to obtain the title compound (39 mg, 93%) as an E/Z mixture.

Workup

  1. extractionfollowed by extraction with ethyl acetate twice
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto yield a residue
  5. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-6b7e61fe82694da6a3fd49512d290b6c
Source dataset
uspto-grants-2015_02
Patent number
US08952003B2

Reaction notes

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