Pyridine → HCID 86593063, compound

HRID 546471Notes

Reaction equation

HRID 546471 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][C@@H:10]1[NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:25][O:26][NH2:27].N1C=CC=CC=1>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C:12](=[N:27][O:26][CH3:25])[CH2:11][C@@H:10]1[NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 68907555HCID 68907555, compound

Product 1

HCID 86593063HCID 86593063, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

cis-N1,N2-Bis(tert-butoxycarbonyl)-4-oxo-1,2-cyclohexanediamine (1.5 g) was dissolved in methanol (30 ml), and O-methylhydroxylamine hydrochloride (572 mg) and pyridine (737 ml) were added to stir the mixture at room temperature for 17 hours. After the reaction mixture was concentrated, water was added to conduct extraction with ethyl acetate. The resultant organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to obtain the title compound (1.52 g) as a colorless solid.

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. additionwater was added
  3. extractionextraction with ethyl acetate
  4. washThe resultant organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-9d00addfeb204dd092429c16832edbca
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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