m-Chloroperbenzoic acid → HCID 53959906, compound

HRID 324872Notes

Reaction equation

HRID 324872 reaction equation
[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)[C:7]([CH:20]=[CH:21][CH2:22][CH2:23][CH3:24])=[C:6]([CH:25]([CH3:27])[CH3:26])[N:5]=1)([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:36])C=1>C(Cl)Cl>[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([S:18]([CH3:19])=[O:36])=[CH:16][CH:17]=2)[C:7]([CH:20]=[CH:21][CH2:22][CH2:23][CH3:24])=[C:6]([CH:25]([CH3:26])[CH3:27])[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54516441HCID 54516441, compound

Product 1

HCID 53959906HCID 53959906, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2,6Diisopropyl-3-hydroxymethyl-4-[4-(methylthio)phenyl]-5-(pent-1-enyl)pyridine (100 mg, 0.261 mmol) (Example 174) was dissolved in methylene chloride (1.5 mL) and stirred at 0° C. under an argon atmosphere. To this mixture was added a solution containing 3-chloroperoxybenzoic add (“mCPBA”) (85%, 53 mg, 0.261 mmol) in methylene chloride (1 mL). The mixture was stirred for 1.5 h at 0° C. and quenched with the addition of a saturated aqueous solution of NaHSO3 (3 mL). The reaction mixture was further diluted through the addition of water (5 mL) and then extracted with methylene chloride (3×10 mL). The combined organic layer was washed sequentially with a saturated aqueous solution of sodium bicarbonate (10 mL) and brine (10 mL), dried (Na2SO4), and concentrated under reduced pressure. The resultant residue was purified by flash chromatography to yield the title compound (52 mg, 50%) as a white solid, mp 133-135° C. 1H NMR (300 MHz, CDCl3): δ 0.77 and 0.69 (t, J=7.5 Hz, 3 H), 1.08-1.36 (m, 14 H), 1.70-1.92 (m, 3 H), 2.75 and 2.76 (s, 3 H), 3.19-3.51 (m, 2 H), 4.32-4.40 (m, 2 H), 5.20-5.45 (m, 1 H), 5.93-6.00 (m, 1 H), 7.31-7.38 (m, 2 H), 7.59-7.70 (m, 2 H). Anal. calc. for C24H33NO2S: C, 71.86; H, 8.29; N, 3.39; S, 7.73. Found: C, 72.14; H, 8.32; N, 3.51; S, 8.02.

Workup

  1. additionTo this mixture was added a solution
  2. additioncontaining 3-chloroperoxybenzoic
  3. stirringThe mixture was stirred for 1.5 h at 0° C.
  4. customquenched with the addition of a saturated aqueous solution of NaHSO3 (3 mL)
  5. additionThe reaction mixture was further diluted through the addition of water (5 mL)
  6. extractionextracted with methylene chloride (3×10 mL)
  7. washThe combined organic layer was washed sequentially with a saturated aqueous solution of sodium bicarbonate (10 mL) and brine (10 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated under reduced pressure
  10. customThe resultant residue was purified by flash chromatography

Sources & evidence

ORD record
ord-78b572f9db6249fa8c960cd1a71a061f
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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