m-Chloroperbenzoic acid → HCID 53977660, compound

HRID 324873Notes

Reaction equation

HRID 324873 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]([CH3:20])=[O:19])=[CH:14][CH:13]=2)[C:7]([CH:21]=[CH:22][CH2:23][CH2:24][CH3:25])=[C:6]([CH:26]([CH3:28])[CH3:27])[N:5]=1)([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:34]>C(Cl)Cl>[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:20])(=[O:34])=[O:19])=[CH:14][CH:13]=2)[C:7]([CH:21]=[CH:22][CH2:23][CH2:24][CH3:25])=[C:6]([CH:26]([CH3:27])[CH3:28])[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53959906HCID 53959906, compound

Product 1

HCID 53977660HCID 53977660, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2,6-Diisopropyl-3-hydroxymethyl-4-[4-(methysulfinyl)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 acid (“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 NaHO3 (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 (31.1 mg, 29%). 1H NMR (300 MHz, CDCl3): δ 0.69 and 0.79 (t, J=7.2 Hz, 3 H), 1.08-1.37 (m, 14 H), 1.45 (t, J=4.2 Hz, 1 H), 1.86-1.93 (m, 2 H), 3.10 and 3.11 (s, 3 H), 3.2-3.50 (m, 2 H), 4.34-4.36 (m, 2 H), 5.20-5.50 (m, 1 H), 5.93-6.00 (m, 1 H), 7.41 (d, J=8.4 Hz, 2 H), 7.96 (d, J=8.4 Hz, 2 H). Anal. calc. for C24H33NO3S: C, 69.28; H, 7.91; N, 3.18; S, 7.50. Found: C, 69.36; H, 8.00; N, 3.37; S, 7.71.

Workup

  1. additionTo this mixture was added a solution
  2. stirringThe mixture was stirred for 1.5 h at 0° C.
  3. customquenched with the addition of a saturated aqueous solution of NaHO3 (3 mL)
  4. additionThe reaction mixture was further diluted through the addition of water (5 mL)
  5. extractionextracted with methylene chloride (3×10 mL)
  6. washThe combined organic layer was washed sequentially with a saturated aqueous solution of sodium bicarbonate (10 mL) and brine (10 mL)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe resultant residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1d531f79779b4c2cbb0f2de3f3ff8ed4
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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