Benzyl Alcohol → HCID 22178579, compound

HRID 993121Notes

Reaction equation

HRID 993121 reaction equation
C([C:4]1[C:5](=[O:13])[NH:6][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:8][CH:9]=1)(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:21])C=CC=CC=1.C([N:33]([CH2:36]C)CC)C.[CH2:38]([OH:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>O1CCOCC1>[CH2:38]([O:45][C:36]([NH:33][C:4]1[C:5](=[O:13])[NH:6][C:7]([CH:10]([CH3:11])[CH3:12])=[CH:8][CH:9]=1)=[O:21])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471Triethylamine2×HCID 199401P,P-Diphenylphosphinic azideHCID 135436702-Oxo-6-(propan-2-yl)-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 22178579HCID 22178579, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Carboxy-6-isopropyl-2(1H)-pyridinone (2.82 g, 15.6 mmol), as prepared in the preceding step, diphenylphosphoryl azide (3.50 mL, 16.2 mmol), and triethylamine (2.30 mL, 16.5 mmol) were refluxed in 1,4-dioxane (100 mL) for 16 hours. Benzyl alcohol (1.65 mL, 15.9 mmol) and additional triethylamine (2.40 mL, 17.2 mmol) were added and the reaction refluxed another 24 hours. After concentrating the reaction mixture in vacuo, the residue was dissolved in methylene chloride, washed with pH 1 brine, saturated NaHCO3, and pH 7 brine, dried over MgSO4, and filtered. The evaporated filtrate was then purified by flash column chromatography (gradient elution, 10% to 25% ethyl acetate in methylene chloride) giving the title compound as a light yellow solid (1.10 g, 25%). 1H NMR (300 MHz, CDCl3) δ 11.61 (br s, 1H), 8.05 (br d, 1H, J=7.2 Hz), 7.67 (s, 1H), 7.39 (m, 5H), 6.08 (d, 1H, J=7.7 Hz), 5.21 (s, 2H), 2.80 (septet, 1H, J=6.9 Hz), 1.28 (s, 3H), 1.26 (s, 3H).

Workup

  1. temperaturethe reaction refluxed another 24 hours
  2. concentrationAfter concentrating the reaction mixture in vacuo
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed with pH 1 brine, saturated NaHCO3, and pH 7 brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe evaporated filtrate was then purified by flash column chromatography (gradient elution, 10% to 25% ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-8201747ea26e4da0abac88936787d1a1
Source dataset
uspto-grants-2002_10
Patent number
US06472399B2

Reaction notes

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