m-Chloroperbenzoic acid → HCID 86593508, compound

HRID 1784157Notes

Reaction equation

HRID 1784157 reaction equation
CN([CH2:4][C@H:5]1[CH:11]=[C:10](SC2C=CC=CC=2)[CH:9]=[CH:8][C@H:7]([CH3:19])[C@@H:6]1[OH:20])C.[CH:21]1[CH:26]=[C:25](Cl)[CH:24]=[C:23](C(OO)=O)[CH:22]=1.[OH:32][S:33]([O-:35])=O.[Na+]>C(Cl)Cl>[C:25]1([S:33]([C:10]2[CH:9]=[CH:8][C@H:7]([CH3:19])[C@H:6]([OH:20])[C:5](=[CH2:4])[CH:11]=2)(=[O:35])=[O:32])[CH:24]=[CH:23][CH:22]=[CH:21][CH:26]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 10017067HCID 10017067, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 86593508HCID 86593508, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of amine 34 (42 mg, 0.14 mmol) in CH2Cl2 (2 mL) was added 140 mg of m-CPBA (0.57 mmol based on 70% content). The mixture was stirred at room temperature for 30 min, then aqueous NaHSO3 was added, the resulting two layers were separated, and the aqueous phase was extracted with CH2Cl2 (3×3 mL). The combined organic layers were washed with saturated aqueous Na2CO3, dried with Na2SO4, and concentrated. The residue was purified by flash column chromatography (EtOAc/hexanes; 1:2) to afford 36 mg (91%) of trienyl sulfone 35. 1H NMR (CDCl3, 300 MHz) δ 7.88-7.92 (m, 2H), 7.54-7.67 (m, 3H), 7.51 (s, 1H), 6.24 (dt, J=11.4 Hz, 1.2 Hz, 1H), 5.90 (dd, J=11.4 Hz, 5.4 Hz, 1H), 5.78 (s, 1H), 5.72(s, 1H), 4.36 (s, 1H), 2.64 (m, 1H), 1.81 (br s, 1H), 1.11 (d, J=7.5 Hz, 3H); 13C NMR (CDCl3, 75 MHz) δ 145.6, 140.2, 139.3, 137.0, 136.1, 133.6, 129.5, 128.1, 128.0, 120.2, 75.1, 39.3, 16.4.

Workup

  1. customthe resulting two layers were separated
  2. extractionthe aqueous phase was extracted with CH2Cl2 (3×3 mL)
  3. washThe combined organic layers were washed with saturated aqueous Na2CO3
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (EtOAc/hexanes; 1:2)

Sources & evidence

ORD record
ord-b21ca584e8cd4b3989e87ac2851e83ab
Source dataset
uspto-grants-2009_03
Patent number
US07501535B2

Reaction notes

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