Pyridine 2-aldoxime → HCID 67284112, compound

HRID 2111673Notes

Reaction equation

HRID 2111673 reaction equation
Cl[O-].[Na+].[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]=[N:11][OH:12].[C:13]([O:17][C:18]([NH:20][CH2:21][C:22]#[CH:23])=[O:19])([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl>[C:13]([O:17][C:18]([NH:20][CH2:21][C:22]1[O:12][N:11]=[C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]=2)[CH:23]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 13395Pyridine 2-aldoximeHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 23665760Sodium Hypochlorite

Product 1

HCID 67284112HCID 67284112, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium hypochlorite (16 ml of a 14% w/v aqueous solution, 29.5 mmol) was added dropwise to a solution of 2-pyridinealdoxime (2 g, 16.4 mmol) and N-tert-butoxycarbonyl-propargylamine (5.6 g, 36.1 mmol) in DCM (30 ml) cooled in an ice bath. The mixture was stirred vigorously and allowed to warm to ambient temperature and stirred for 18 hours. The aqueous layer was separated and extracted with DCM. The combined organic extracts were combined, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography on silica gel eluting with diethyl ether/isohexane (1:1) to give the title compound (1.93 g, 43%). NMR (CDCl3) 1.45 (s, 9H), 4.5 (m, 2H), 5.03 (bs, 1H), 6.8 (s, 1H), 7.35 (m, 1H), 7.8 (m, 1H), 8.05 (d, 1H), 8.67 (m, 1H).

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirred for 18 hours
  3. customThe aqueous layer was separated
  4. extractionextracted with DCM
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by column chromatography on silica gel eluting with diethyl ether/isohexane (1:1)

Sources & evidence

ORD record
ord-9cbc9e5537ab47cebd4e174e31e71e67
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

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